Benzyl chloroformate → Benzyl 4-cyanopiperidine-1-carboxylate

HRID 2256036Notes

Reaction equation

HRID 2256036 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)#[N:2].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]>C(=O)([O-])[O-].[Na+].[Na+]>[CH2:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]1)=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 1382234-Cyanopiperidine

Product 1

HCID 22028286Benzyl 4-cyanopiperidine-1-carboxylateYield 86.9%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

A solution of 4-cyanopiperidine (5.00 g) in 10% aqueous sodium carbonate solution (100 mL) was cooled to 0° C. and treated dropwise with benzyl chloroformate (9.30 g). The resulting mixture was warmed to room temperature and stirred for 16 hours. The biphasic mixture was extracted with ethyl acetate. The organic extracts were washed with water and brine, combined, dried, filtered and evaporated. The resulting oil was purified by chromatography, with ethyl acetate:hexane (gradient 1:4, 1:2) as eluent, to give the protected piperidine as a clear oil (9.64 g); MS: m/z=245(M+1); NMR (CDCl3): 7.35 (m, 5), 5.13 (s, 2), 3.71 (m, 2), 3.44 (m, 2), 2.81 (m, 1), 1.88-1.60 (m, 4).

Workup

  1. extractionThe biphasic mixture was extracted with ethyl acetate
  2. washThe organic extracts were washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oil was purified by chromatography, with ethyl acetate

Sources & evidence

ORD record
ord-2a05ce02d9c3427e80c5bd9cd3ccf604
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

Loading…