Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

HRID 1379111Notes

Reaction equation

HRID 1379111 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-03a242f28ae04623bd3034d0fb0b0cb7
Source dataset
uspto-grants-1997_09
Patent number
US05670515

Reaction notes

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