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

HRID 1593024Notes

Reaction equation

HRID 1593024 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:21](Cl)(=[O:23])[CH3:22]>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:21](=[O:23])[CH3:22])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 4158521-Benzyl-4-piperidylamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzylpiperidin-4-amine (10 g) in dichloromethane (80 ml), cooled to 5° C., was added pyridine (5.1 ml) followed by acetyl chloride (4.5 ml) and the resulting mixture was stirred for 5 hours. The reaction mixture was washed with 1N NaOH (×2) and then the organic layers were dried and evaporated to dryness to give a solid which was recrystallised from ethyl acetate to give N-(1-benzylpiperidin-4-yl)acetamide. Yield 8.8 g. NMR (d6 DMSO): 1.4 (m, 2H), 1.7 (m, 2H), 1.8 (s, 3H), 2.0 (m, 2H), 2.75 (m, 2H), 3.45 (s, 2H), 3.55 (m, 1H), 7.3 (m, 5H), 7.75 (d, 1H).

Workup

  1. washThe reaction mixture was washed with 1N NaOH (×2)
  2. customthe organic layers were dried
  3. customevaporated to dryness
  4. customto give a solid which
  5. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-2c3b7a1fe9784fd4853709a01074e011
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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