[ CAS No. 498-95-3 ] {[proInfo.proName]}

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Quality Control of [ 498-95-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 498-95-3 ]

SDS Specification

Alternatived Products of [ 498-95-3 ]

Product Details of [ 498-95-3 ]

CAS No. :	498-95-3	MDL No. :	MFCD00005992
Formula :	C₆H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	129.16	Pubchem ID :	-
Synonyms :	(±)-β-Homoproline;Hexahydronicotinic acid;DL-Piperidine 3-Carboxylic Acid;3-Piperidine Carboxylic Acid;(R,S)-Nipecotic Acid;(±)-Nipecotic Acid;3-Carboxypiperidine	Chemical Name :	Piperidine-3-carboxylic acid

Calculated chemistry of [ 498-95-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	37.33
TPSA :	49.33 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.99
Log Po/w (XLOGP3) :	-2.89
Log Po/w (WLOGP) :	-0.31
Log Po/w (MLOGP) :	0.0
Log Po/w (SILICOS-IT) :	0.46
Consensus Log Po/w :	-0.35

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	1.25
Solubility :	2280.0 mg/ml ; 17.6 mol/l
Class :	Highly soluble
Log S (Ali) :	2.41
Solubility :	33300.0 mg/ml ; 258.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.42
Solubility :	48.5 mg/ml ; 0.376 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.68

Safety of [ 498-95-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 498-95-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 498-95-3 ]
Downstream synthetic route of [ 498-95-3 ]

[ 498-95-3 ] Synthesis Path-Upstream 1~2

1
[ 82911-69-1 ]
[ 498-95-3 ]
[ 193693-68-4 ]

Reference： [1] Journal of Organic Chemistry, 2004, vol. 69, # 23, p. 8077 - 8085

2
[ 82911-69-1 ]
[ 498-95-3 ]
[ 193693-68-4 ]
[ 193693-67-3 ]

Reference： [1] Helvetica Chimica Acta, 2005, vol. 88, # 8, p. 2235 - 2249

[ 498-95-3 ] Synthesis Path-Downstream 1~11

1
[ 501-53-1 ]
[ 498-95-3 ]
[ 78190-11-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydroxide;	C. 1,3-Piperidinedicarboxylic acid, 1-(phenylmethyl)ester Benzyl chloroformate (4 mL) was added dropwise to a cooled (0-5 C.), stirred solution of piperidine-3-carboxylic acid (1.03 g, 8 mmol) in 1 N aqueous NaOH solution (25 mL). During the twenty minute addition, the pH was maintained between 8 and 9 by addition of 1 N NaOH solution. After addition was complete, the mixture was stirred cold for an additional hour, maintaining the pH thoughout this period. The reaction mixture was then extracted with ether (240 mL). The ether extracts were discarded and the aqueous layer was acidified with 1 N HCl solution. The acidified aqueous layer was then extracted with dichloromethane (240 mL). The combined extracts were dried over magnesium sulfate and concentrated in vacuo to give title acid as a viscous oil (1.73 g, 82%).
113%	In diethyl ether; water;	Example 437A N-Benzyloxycarbonyl nipecotic acid To a solution of nipecotic acid 10 g, 63.6 mmol) in 1 N NaOH (2.5 g in 64 mL water, 63.6 mmol) at 0 C. was alternately added benzyloxycarbonyl chloride (10.9 mL, 76.5 mmol) in diethyl ether (50 mL) and 1 N NaOH (5 g in 128 mL water, 127.2 mmol) in five portions. The reaction mixture was stirred at 0 C. for 2 hours, and at ambient temperature for 24 hours. Then this was made acidic with 10% HCl and the solid formed was filtered and dried (vacuum oven, 45 C.) to obtain the title compound (18.9 g, 113%). MS (ESI) m/e 264 (M+H)+.
		Example 153 A1-(benzyloxycarbonyl)piperidine-3-carboxylic acid; To the solution of piperidine-3-carboxylic acid (1.3 g, 10 mmol) in water (20 mL) was added sodium hydroxide (1.6 g, 40 mmol). Then benzyloxycarbonyl chloride (2.02 g, 12 mmol) was added dropwise at 0 C. The mixture was stirred at 0 C. for 2 h. The resulting mixture was treated with 5N hydrochloric acid to pH=6 and extracted with ethyl acetate, the solvent was removed under reduced pressure and dried in vacuum. 2.2 g of solid of 1-(benzyloxycarbonyl)piperidine-3-carboxylic acid was obtained. LC-MS (ESI) m/z: 264 (M+1)+.

		[1246] To a solution of nipecotic acid (10 g, 63.6 mmol) in 1 N NaOH (2.5 g in 64 mL water, 63.6 mmol) at 0 C. was alternately added benzyloxycarbonyl chloride (10.9 mL, 76.5 mmol) in diethyl ether (50 mL) and 1 N NaOH (5 g in 128 mL water, 127.2 mmol) in five portions. The reaction mixture was stirred at 0 C. for 2 h, and at ambient temperature for 24 h. Then this was made acidic with 10% HCl and the solid formed was filtered and dried (vacuum oven, 45 C.) to obtain the title compound (18.9 g, 113%). MS (ESI) m/e 264 (M+H)+.
		EXAMPLE 15 ()-BENZYL 3- (6-METHOXY-2-METHYL-1-OXO-4-PHENYL-1, 2-DIHYDROISOQUINOLIN-3-YL) PIPERIDINE-1- carboxylate; Step A: ()-L-F (BENZYLOXY) CARBONYLLPIPERIDINE-3-CARBOXYLIC ACID; To an ice cooled solution of nipecotic acid (10.0 g, 77.5 mmol), sodium hydroxide (3.4 g, 85 mmol), and tetrahydrofuran (50 ML) in water (100 ML) was added by simultaneous dropwise addition benzylchloroformate (13.3 ML, 93 mmol) in tetrahydrofuran (50 ML) and sodium hydroxide (3.4 g, 85 mmol) in water (50 mL). Warmed slowly to room temperature. After 24 hours tetrahydrofuran was removed in vacuo and the resulting aqueous mixture acidified with 3 N hydrochloric acid and extracted with dichloromethane (3X). The combined organic portions were dried with anhydrous magnesium sulfate. Filtration followed by evaporation of the filtrate in vacuo gave the titled COMPOUND. HNMR (CHCIS, 300MHZ) Q 7.45-7. 20 (m, 5H) ; 5.14 (m, 2H); 4.21 (br S, 1H) ; 3.96 (m, 1H), 3.15 (br s, 1H) ; 2.93 (m, 1H) ; 2.51 (m, 1H) ; 2.09 (m, 1H); 1.80-1. 60 (m, 2H); 1.50 (m, 1H) ppm
		To a stirred solution of 3-piperidine carboxylic acid (1.48 g, 11.5 mmol) and saturated sodium bicarbonate (40 mL) in tetrahydrofuran (40 mL) at 0 C. was added benzylchloroformate (2.05 g, 12.0 mmol). The mixture was stirred in an ice-bath for 3 h, and then at room temperature for 16 h. The mixture was then cooled to 0 C. and the pH was reduced to ca. 1.0 with 6 M HCl. The mixture was extracted three times with ethyl acetate. The combined extracts were dried with magnesium sulfate, filtered, and concentrated to provide 10.0 g of the title compound as a colorless oil.
		Step 1. 1-(Benzyloxycarbonyl)piperidine-3-carboxylic; A 500-mL 4-necked round-bottom flask was charged with a solution of NaOH (8 g, 198.00 mmol, 1.00 equiv, 99%) in H2O (200 mL). To this was added piperidine-3-carboxylic acid (25.8 g, 197.75 mmol, 1.00 equiv, 99%), in small portions at 0 C. Then, a solution of benzyl carbonochloridate (39.2 g, 227.48 mmol, 1.15 equiv, 99%) in Et2O (50 mL) was added at 0 C. over 40 minutes. Then a solution of NaOH (12 g, 1.50 equiv) in H2O (300 mL) was added drop wise with stirring at 0-10 C. The resulting solution was allowed to stir overnight at room temperature. The reaction progress was monitored by TLC (EtOAc/PE=1/1). The pH adjusted to 3 with 10% aqueous HCl. The resulting solution was extracted with ethyl acetate (3×500 mL). Combined organic layers were dried over anhydrous magnesium sulfate and concentrated on a rotary evaporator to afford 1-(benzyloxycarbonyl)piperidine-3-carboxylic acid (58 g) as white solid.
	With sodium hydroxide; In water; at 0 - 20℃;	Step 1: In a 100 ml three-necked flask, in a stream of nitrogen and under magnetic stirring the nipecotinic acid (3.7 g) was placed in solution in a 3N sodium hydroxide solution (30 ml). The solution was cooled over an ice bath to 0 C. Benzyl chloroformiate (5.8 ml) was added in fractions at 0 C. alternately with a 3N sodium hydroxide solution (9.3 ml) for a time of 45 min. After the addition time the reaction medium was pale yellow and the temperature 3 C. The ice bath was removed and the reaction medium left under stirring at ambient temperature overnight. The aqueous phase was then extracted once with ethyl ether, then acidified to pH 1 using a 3N hydrochloric acid solution. The acidified aqueous phase was extracted three times with ethyl ether. The ether extract phase was successively washed with 1N hydrochloric acid solution, then twice with saturated sodium chloride solution before being dried over magnesium sulphate, filtered then concentrated in vacuo. [0126] The yellow oil obtained (7.35 g, 98%) was used at the following step without any purification step.

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 1297 - 1300
[2]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 397 - 416
[3]Patent: US5583146,1996,A
[4]Patent: US6878700,2005,B1
[5]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 71
[6]Patent: US2004/116518,2004,A1 .Location in patent: Page 117
[7]Patent: WO2005/30726,2005,A1 .Location in patent: Page/Page column 20; 31
[8]Patent: US2006/19975,2006,A1 .Location in patent: Page/Page column 21
[9]Patent: US8080566,2011,B1 .Location in patent: Page/Page column 30
[10]Patent: US2014/315950,2014,A1 .Location in patent: Paragraph 0125-0126

2
[ 498-95-3 ]
[ 174543-74-9 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 1297 - 1300

3
[ 1184-90-3 ]
[ 498-95-3 ]
N-amidino-3-carboxylglycyl-L-aspartyl-L-valine [ No CAS ]
[ 136483-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water;	A. 2.5 g nipecotic acid was stirred with a solution of 2.67 g potassium carbonate in 20 ml of water to give a clear solution. To this solution wasadded 2.4 g <strong>[1184-90-3]aminoiminomethanesulfonic acid</strong> in small portions over a period of 10 minutes. The solution was allowed to stand overnight and the resulting precipitate recrystallized from water to give N-amidino-piperidine-3-carboxylic acid.

Reference： [1]Patent: US5051405,1991,A

4
[ 4138-26-5 ]
[ 88495-55-0 ]
[ 498-95-3 ]
[ 498-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	With Cupriavidus sp. KNK-J915 strain (FERM BP-10739); at 30℃; for 35h;pH 7;Aqueous phosphate buffer; Enzymatic reaction;Product distribution / selectivity;	Example 3 Selective Hydrolysis of R-Enantiomer in Racemic <strong>[4138-26-5]Nipecotamide</strong>Cupriavidus sp. KNK-J915 strain (FERM BP-10739) was cultivated by the method of Example 1 to prepare a bacterial cell suspension. The bacterial cell suspension (0.1 ml) was mixed with 100 mM phosphate buffer containing 1.0 to 5.0percent of racemic <strong>[4138-26-5]nipecotamide</strong> (0.1 ml, pH 7.0), and the mixture was shaken at 30° C. for 35 hours. After completion of the reaction, solid substance such as bacterial cells was removed by centrifugal separation, and then a substrate and a product in the reaction mixture were reacted with benzyl chlorocarbonate for derivatization. The resulting derivative was analyzed by high performance liquid chromatography to determine the conversion rate (percent) and optical purity (ee percent). The results are listed in Table 3.High Performance Liquid Chromatographic Analysis ConditionsAnalysis of Conversion RateColumn: YMC-A303 (4.6 mm.x.250 mm, manufactured by YMC Inc., Eluent: 20 mM phosphoric acid aqueous solution (pH 2.5)/acetonitrile=7/3, Flow rate: 1.0 ml/minute, Column temperature: 35° C., Measuring wavelength: 210 nmAnalysis of Optical PurityColumn: CHIRALPAK AD-RH (4.6 mm.x.150 mm, manufactured by Daicel Chemical Industries, Ltd.), Eluent: 20 mM phosphate buffer (pH 2.5)/acetonitrile=7/3, Flow rate: 0.5 ml/minute, Column temperature: room temperature, Measuring wavelength: 210 nm

Reference： [1]Patent: US2010/105917,2010,A1 .Location in patent: Page/Page column 15

5
[ 4138-26-5 ]
(R)-piperidine-3-carboxamide [ No CAS ]
[ 498-95-3 ]
[ 498-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; at 30℃; for 60h;pH 7;Aqueous phosphate buffer; Enzymatic reaction;	Example 4Selective Hydrolysis of S-enantiomer in Racemic <strong>[4138-26-5]Nipecotamide</strong>Cupriavidus sp. KNK-J915 strain (FERM BP-10739) was cultivated by the method of Example 2 to obtain a 20-fold concentrated bacterial cell suspension. To the bacterial cell suspension (100 ml), racemic <strong>[4138-26-5]nipecotamide</strong> (19.9 g) was added. After the pH of the mixture was adjusted to 7 using NaOH, the mixture was shaken at 30° C. for 60 hours. After completion of the reaction, the reaction mixture was heat-treated at 70° C. for 30 minutes, and solid substance such as bacterial cells was removed by centrifugal separation. The substrate and product in the reaction mixture were analyzed by the method of Example 3; as a result, the conversion rate was 52.7percent, the optical purity of (R)-<strong>[4138-26-5]nipecotamide</strong> was 98.8percent ee and the optical purity of (S)-<strong>[4138-26-5]nipecotamide</strong> was 88.1percent ee.

Reference： [1]Patent: US2010/105917,2010,A1 .Location in patent: Page/Page column 15-16

6
[ 3537-14-2 ]
[ 498-95-3 ]
C₁₁H₁₃N₅O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5896 - 5899

7
[ 498-95-3 ]
[ 91419-49-7 ]

Reference： [1]Patent: WO2014/149164,2014,A1

8
[ 4138-26-5 ]
(R)-piperidine-3-carboxamide [ No CAS ]
[ 498-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	With amidase from Cupriavidus sp. KNK-J915 (FERM BP-10739); water; In aq. phosphate buffer; at 30℃;pH 7;Enzymatic reaction;	General procedure: During the purification and characterization of amidase from Cupriavidus sp. KNK-J915, an enzyme assay was performed with (R,S)-BNPD as a substrate. The standard reaction mixture (0.2 mL) contained 100 mM potassium phosphate buffer (pH 7.0), 45.8 mM BNPD, and an appropriate amount of the enzyme. After the reaction was performed at 30°C for 0.5?1 h, the amount of BNPA was determined using HPLC. One unit of the enzyme was defined as the amount catalyzing the formation of 1 mol of BNPA per minute under the aforementioned condition. Protein content was determined by the Bradford method [11] with BSA as a standard using a kit from Bio-Rad Laboratories Ltd. (Tokyo, Japan).

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2014,vol. 109,p. 136 - 142

9
[ 4138-26-5 ]
[ 88495-55-0 ]
(R)-piperidine-3-carboxamide [ No CAS ]
[ 498-95-3 ]
[ 498-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	With amidase from Cupriavidus necator JMP134; water; In aq. phosphate buffer; at 30℃;pH 7;Enzymatic reaction;	General procedure: During the purification and characterization of amidase from Cupriavidus sp. KNK-J915, an enzyme assay was performed with (R,S)-BNPD as a substrate. The standard reaction mixture (0.2 mL) contained 100 mM potassium phosphate buffer (pH 7.0), 45.8 mM BNPD, and an appropriate amount of the enzyme. After the reaction was performed at 30°C for 0.5?1 h, the amount of BNPA was determined using HPLC. One unit of the enzyme was defined as the amount catalyzing the formation of 1 mol of BNPA per minute under the aforementioned condition. Protein content was determined by the Bradford method [11] with BSA as a standard using a kit from Bio-Rad Laboratories Ltd. (Tokyo, Japan).

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2014,vol. 109,p. 136 - 142

10
[ 498-95-3 ]
[ 7583-53-1 ]

Reference： [1]Patent: WO2016/144844,2016,A1

11
[ 498-95-3 ]
[ 194726-40-4 ]

Reference： [1]Patent: CN109988098,2019,A

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Isomers

Technical Information

? Arndt-Eistert Homologation ? Hunsdiecker-Borodin Reaction ? Passerini Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Carboxylic Acids ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction

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H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 498-95-3 ] {[proInfo.proName]}

Quality Control of [ 498-95-3 ]

Related Doc. of [ 498-95-3 ]

Product Details of [ 498-95-3 ]

Calculated chemistry of [ 498-95-3 ] Expand+

Physicochemical Properties

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Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 498-95-3 ]

[ 498-95-3 ] Synthesis Path-Upstream 1~2

[ 498-95-3 ] Synthesis Path-Downstream 1~11

Technical Information

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Physical hazards

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