Triethylamine → Benzyl 4-oxopiperidine-1-carboxylate

HRID 1926644Notes

Reaction equation

HRID 1926644 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>ClCCl>[O:8]=[C:5]1[CH2:6][CH2:7][N:2]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 30848514-Piperidone hydrochloride

Product 1

HCID 643496Benzyl 4-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of piperidin-4-one hydrochloride (1567 g, 11.56 mol) and triethylamine (1400 g, 13.87 mol) in dichloromethane (12 L) was added benzyl chloroformate (1965 g, 11.55 mol) dropwise at 0° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. TLC (EtOAc/petroleum ether=1:5) showed the reaction was complete. The mixture was washed with water (3 L) and brine (1 L), dried over sodium sulfate and concentrated to afford benzyl 4-oxopiperidine-1-carboxylate as a colorless oil.

Workup

  1. additionAfter the addition
  2. washThe mixture was washed with water (3 L) and brine (1 L)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa014a24a65e42518c3de4845d1feb09
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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