Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

HRID 1768721Notes

Reaction equation

HRID 1768721 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[OH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>ClCCl>[CH2:12]([O:11][C:9]([N:23]1[CH2:24][CH2:25][CH:20]([OH:19])[CH2:21][CH2:22]1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 79341Piperidin-4-ol

Product 1

HCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

69.1 ml of triethylamine and 70.2 ml of benzyl chloroformate are added in succession at 0° C. to a solution of 50 g of 4-hydroxypiperidine in 500 ml of dichloromethane. The resulting suspension is stirred at room temperature overnight and subsequently filtered. The residue which separates after concentration of the filtrate is taken up in ethyl acetate, washed with water and 1N hydrochloric acid, dried and concentrated. There are obtained 73.6 g of N-benzyloxycarbonyl-4-hydroxy-piperidine. Rf =0.56 (ethyl acetate/methanol 9:1), MS (EI): 235 (M+).

Workup

  1. filtrationsubsequently filtered
  2. washwashed with water and 1N hydrochloric acid
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bbc82c01f6714546a39520fd71994fb0
Source dataset
uspto-grants-1995_01
Patent number
US05378712

Reaction notes

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