Ethyl chloroformate → ethyl N-(1-benzylpiperidin-4-yl)carbamate

HRID 1090691Notes

Reaction equation

HRID 1090691 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1>N1C=CC=CC=1>[C:15]1([CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([NH:7][C:2](=[O:3])[O:4][CH2:5][CH3:6])[CH2:9][CH2:10]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 12641845ethyl N-(1-benzylpiperidin-4-yl)carbamateYield 62.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl chloroformate (30 g, 0.276 mol) was added at 0° C. to 4-amino-1-phenylmethylpiperidine (50 g, 0.262 mol) in pyridine (600 mL). After the addition, the mixture was kept at room temperature overnight, and the pyridine was then evaporated. The residue was extracted with methylene chloride; and the resulting solution washed with water, dried over sodium sulfate, and the methylene chloride evaporated to dryness. The residue was dissolved in diisopropyl ether. A white product precipitated, which was isolated by filtration to yield 42.71 g (62%) of ethyl (1-phenylmethyl-4-piperidyl)-carbamate, m.p. 100° C.

Workup

  1. additionAfter the addition
  2. customthe pyridine was then evaporated
  3. extractionThe residue was extracted with methylene chloride
  4. washand the resulting solution washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe methylene chloride evaporated to dryness
  7. dissolutionThe residue was dissolved in diisopropyl ether
  8. customA white product precipitated
  9. customwhich was isolated by filtration

Sources & evidence

ORD record
ord-0fe390e75e8e454c8ded6931d2c958fc
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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