Triethylamine → Ethyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1614332Notes

Reaction equation

HRID 1614332 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>ClC(Cl)Cl>[OH:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4207714-Piperidinemethanol

Product 1

HCID 19773576Ethyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 67 parts of 4-piperidinemethanol, 61 parts of N,N-diethylethanamine and 750 parts of trichloromethane there were added dropwise 64.5 parts of ethyl chloroformate. Stirring was continued for 2 hours at reflux temperature. After cooling, the reaction mixture was washed with water, dried, filtered and evaporated, yielding 75 parts (70%) of ethyl 4-(hydroxymethyl)-1-piperidinecarboxylate (interm. 50).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7af589cdcea1485eb185dcafeb158da0
Source dataset
uspto-grants-1993_03
Patent number
US05196535

Reaction notes

Loading…