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Chemical Structure| 837-52-5 Chemical Structure| 837-52-5
Chemical Structure| 837-52-5

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CAS No.: 837-52-5

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Product Details of 7-Chloro-4-(piperazin-1-yl)quinoline

CAS No. :837-52-5
Formula : C13H14ClN3
M.W : 247.72
SMILES Code : C1=C(Cl)C=C2C(=C1)C(=CC=N2)N3CCNCC3
MDL No. :MFCD01476123
InChI Key :DNXNPMDUDGUXOB-UHFFFAOYSA-N
Pubchem ID :738389

Safety of 7-Chloro-4-(piperazin-1-yl)quinoline

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Application In Synthesis of 7-Chloro-4-(piperazin-1-yl)quinoline

* 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.

  • Downstream synthetic route of [ 837-52-5 ]

[ 837-52-5 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 135865-78-0 ]
  • [ 837-52-5 ]
  • [ 1114997-28-2 ]
  • 2
  • [ 401564-36-1 ]
  • [ 837-52-5 ]
  • [ 401567-71-3 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of 7a (450 mg, 1.50 mmol), 1-(4-chloroisoquinolin-1-yl)piperazine (446 mg, 1.80 mmol) and acetic acid (0.090 mL, 1.6 mmol) in 1,2-dichloroethane (8 mL) was added sodium triacetoxyborohydride (636 mg, 3.00 mmol) and the mixture was stirred at room temperature for 3 h. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with brine, dried and concentrated under reduced pressure. The residue purified by silica gel chromatography with chloroform/methanol (50:1, v/v) to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(4-chloroisoquinolin-1-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine (596 mg, 75%) as a white powder.The above compound (592 mg, 1.11 mmol) was dissolved in 1.1 mol/L hydrogen chloride in methanol (10 mL), and the mixture was stirred at room temperature for 5 days. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized with ethanol to give the title compound (318 mg, 52%) as a pale-yellow powder.
  • 3
  • [ 2895-21-8 ]
  • [ 837-52-5 ]
  • 2-(4-(7-chloroquinolin-4-yl)piperazine-1-yl)-N-isopropylacetamide [ No CAS ]
  • 4
  • [ 19047-31-5 ]
  • [ 837-52-5 ]
  • 2-(4-(7-chloroquinolin-4-yl)piperazine-1-yl)-N-cyclopropylacetamide [ No CAS ]
  • 5
  • [ 3034-48-8 ]
  • [ 837-52-5 ]
  • 7-chloro-4-(-4-(5-nitrothiazol-2-yl)piperazin-1-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With sodium hydrogencarbonate; In ethanol; for 0.5h;Reflux; A mixture of 0.35 g 7-chloro-4-(piperazin-1-yl)quinoline(13, 1.4 mmol), 0.29 g <strong>[3034-48-8]<strong>[3034-48-8]2-bromo-5-nitrothiazol</strong>e</strong> (12, 1.4 mmol) and 0.12 g sodium bicarbonate (1.4 mmol) in3 cm3 ethanol was stirred under reflux for 30 min. The reaction mixture was then cooled to room temperature and the precipitate was filtered, washed with ethanol, water, glacial acetic acid, and then with small portions of water to give a pure brown solid 19. Yield: 0.53 g (71.0 percent); m.p.:251-256 °C; 1H NMR (500 MHz, DMSO-d6): d = 3.30 (s,8H, H-200), 7.10 (d, J = 5.0 Hz, 1H, H-3), 7.60 (dd,J = 2.2, 9.0 Hz, 1H, H-6), 8.00 (d, J = 2.2 Hz, 1H, H-8),8.10 (d, J = 9.0 Hz, 1H, H-5), 8.50 (s, 1H, H-40), 8.80 (d,J = 5.0 Hz, 1H, H-2) ppm; 13C NMR (125 MHz, DMSOd6):d = 51.1 (C-200), 110.5 (C-50), 121.8 (C-3), 126.5 (C-4a), 128.6 (C-6), 134.3 (C-8), 136.8 (C-40), 147.8 (C-7),150.1 (C-8a), 152.7 (C-2), 156.1 (C-20), 172.9 (C-4) ppm;HRMS (ESI): m/z calcd for C16H15N5O2S [M?H]?376.06350, found 376.06295.
  • 6
  • [ 3034-47-7 ]
  • [ 837-52-5 ]
  • 7-chloro-4-(-4-(5-nitrothiazol-2-yl)piperazin-1-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.3% With potassium carbonate; In acetonitrile; at 30 - 80℃; for 1.0h; General procedure: To a suspension of 7-chloro-4-(piperazin-1-yl)quinoline (1mmol) and potassium carbonate (1.5mmol) in acetonitrile was added the corresponding alkyl halide (1mmol) at 30°C. The reaction mixture was then heated to 80°C for 1h (monitored by TLC and LCMS for completion) and cooled to 30°C. The mixture was then filtered through celite bed, and acetonitrile was evaporated in vacuo. The resultant residue was diluted with water and dichloromethane, and the layers separated. The aqueous layer was re-extracted with dichloromethane (2×5mL). The combined organic extract was washed with brine, dried over sodium sulphate and evaporated in vacuo.
 

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