Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

HRID 2257909Notes

Reaction equation

HRID 2257909 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-f72f4889289b458da4d2812d081d69ef
Source dataset
uspto-grants-1997_08
Patent number
US05658928

Reaction notes

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