Triethylamine → Benzyl piperidine-1-carboxylate

HRID 1076

Reaction equation

HRID 1076 reaction equation
O[CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(CC)CC.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(Cl)(Cl)Cl.CO>C(Cl)Cl>[C:16]([N:5]1[CH2:6][CH2:7][CH2:2][CH2:3][CH2:4]1)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 79341Piperidin-4-olHCID 21584188Chloroform methanol

Product 1

HCID 228749Benzyl piperidine-1-carboxylateYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Hydroxypiperidine (10.8 g, 107 mmol) and Et3N (17 mL, 123 mmol) in 80 mL of CH2Cl2 was cooled in an ice bath whereupon benzyl chloroformate (16.3 mL, 114 mmol) was added. After stirring 1.5 h at R.T. the mixture was subjected to standard work-up conditions to give 13.9 g (55%) of N-Cbz-piperidine after chromatography (CHCl3 /MeOH; 10:1). [1H]-NMR(CDCl3) consistent with structure.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-554bd9dd465641989667d60605d8d5a8
Source dataset
uspto-grants-1998_03
Patent number
US05723490

Linked notes

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