Triethylamine → 1-Benzyloxycarbonyl-3-piperidone

HRID 650968Notes

Reaction equation

HRID 650968 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(Cl)Cl.C(OCC)(=O)C>[CH2:19]([O:18][C:16]([N:1]1[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 33722Piperidin-3-one

Product 1

HCID 15141691-Benzyloxycarbonyl-3-piperidone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-piperidone (12 mmol) in 200 mL of methylene chloride. is added triethylamine (18 mmol) in a single portion at room temperature and the reaction mixture cooled to 0° C. Benzyl chloroformate (12 mmol) is added dropwise via addition funnel and the reaction mixture allowed to warm to room temperature. Stirring is continued for 2 hours at room temperature. The reaction mixture is diluted with ethyl acetate (200 mL) and washed with 1N hydrochloric acid (3×100 mL), water and brine. The organic layer is worked up to provide N-Benzyloxycarbonyl-3-piperidone.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with 1N hydrochloric acid (3×100 mL), water and brine

Sources & evidence

ORD record
ord-b80596e8795847d2a8083ccfffd02bdf
Source dataset
uspto-grants-2001_08
Patent number
US06277865B1

Reaction notes

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