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Chemical Structure| 85817-34-1 Chemical Structure| 85817-34-1

Structure of 85817-34-1

Chemical Structure| 85817-34-1

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CAS No.: 85817-34-1

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Product Details of [ 85817-34-1 ]

CAS No. :85817-34-1
Formula : C12H18N2O
M.W : 206.28
SMILES Code : OCC1CN(CC2=CC=CC=C2)CCN1
MDL No. :MFCD03001699
InChI Key :PJMFGDYBTJEEDP-UHFFFAOYSA-N
Pubchem ID :2756656

Safety of [ 85817-34-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 85817-34-1 ]

* 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 [ 85817-34-1 ]

[ 85817-34-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 149648-71-5 ]
  • [ 85817-34-1 ]
References: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2075 - 2083.
[2] Patent: WO2010/124042, 2010, A2, . Location in patent: Page/Page column 129.
  • 2
  • [ 181955-94-2 ]
  • [ 584-08-7 ]
  • [ 7757-82-6 ]
  • [ 85817-34-1 ]
YieldReaction ConditionsOperation in experiment
78% With sodium cyanoborohydride; benzaldehyde; acetic acid In tetrahydrofuran; methanol 3.
4-Benzyl-2-hydroxymethylpiperazine
To a cooled (0° C.) and stirred solution of Intermediate 1 (22 g, 57 mmol), acetic acid (9.7 mL, 171 mmol) and sodium cyanoborohydride (7.16 g, 114 mmol) in methanol (440 mL) was added benzaldehyde (5.8 mL, 57 mmol).
The cooling bath was removed and the mixture stirred at room temperature for 3 h.
Saturated K2 CO3 solution (200 mL) was added and the mixture stirred for 15 min.
The solvents were evaporated and the residue partitioned between CH2 Cl2 (2*400 mL) and water (500 mL).
The combined organic layers were dried (Na2 SO4) and evaporated.
The residue was chromatographed on silica gel, eluding with CH2 Cl2: MeOH (95:5) to afford an inseparable mixture of 4-benzylpiperazine-2-carboxylic acid methyl ester and the corresponding ethyl ester (5.33 g, 40percent), in a 7:1 ratio respectively.
To a solution of the esters (5.33 g, 22.8 mmol) in THF (200 mL) was added LiAl H4 (22.8 mL of a 1.0M solution in ether) dropwise at -10° C.
Stirring was continued at -10° C. for 2.5 h.
After this time saturated Na2 SO4 solution (30 mL) was added and the cooling bath removed.
Stirring was continued at room temperature for 10 min then the mixture was filtered and the filtrate evaporated.
The residue was chromatographed on silica gel, eluding with CH2 Cl2:MeOH:NH3 (90:8:1-->60:8:1) to afford the title compound (3.7 g, 78percent) as a colourless oil. 1 H NMR (360 MHz, CDCl3) δ 1.89-1.95 (1H, m), 2.08-2.30 (3H, m), 2.68-2.71 (2H, m), 2.86-3.04 (3H, m), 3.45-3.60 (4H, m), 7.13-7.32 (5H, m). MS (ES+) 207 (M+1).
References: [1] Patent: US5849746, 1998, A, .
  • 3
  • [ 149648-70-4 ]
  • [ 85817-34-1 ]
References: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2075 - 2083.
  • 4
  • [ 140-28-3 ]
  • [ 85817-34-1 ]
References: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2075 - 2083.
  • 5
  • [ 936553-15-0 ]
  • [ 85817-34-1 ]
References: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2851 - 2854.
 

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