Water → N-(1-Benzylpiperidin-4-yl)acetamide

HRID 2228

Reaction equation

HRID 2228 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.C(N(CC)CC)C.O>ClCCl>[C:1]([NH:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 12641850N-(1-Benzylpiperidin-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (3.95 ml) was added dropwise to a stirred solution of 4-amino1-benzylpiperidine (10.0 g) and triethylamine (7.7 ml) in dry dichloromethane (100 ml) at 4° C. The mixture was allowed to reach ambient temperature and stirred for 16 hours. Water was then added, the organic phase separated and dried (MgSO4), and removal of the solvent by evaporation gave 4-acetylamino-1-benzylpiperidine, 10.23 g, as a light brown solid which was used without further purification: NMR (CDCl3) δ 7.29(5H,m), 5.29(1H,b), 3.79(1H,m), 3.49(2H,s), 2.80(2H,dm), 2.12(2H,dt), 1.95(3H,s), 191(2H,dm), 1.46(2H,dq); m/e 233 (M+H)+.

Workup

  1. customto reach ambient temperature
  2. customthe organic phase separated
  3. customdried
  4. custom(MgSO4), and removal of the solvent
  5. customby evaporation

Sources & evidence

ORD record
ord-53468aff36b74b69af45a0218b9d4c73
Source dataset
uspto-grants-1998_03
Patent number
US05728701

Linked notes

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