1-Chloroethyl chloroformate → 4-(2-Chlorophenyl)-4-methylpiperidine

HRID 242618Notes

Reaction equation

HRID 242618 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])([CH3:14])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:11]1([CH3:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 23136891HCID 23136891, compound

Product 1

HCID 231369824-(2-Chlorophenyl)-4-methylpiperidineYield 73.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1-benzyl-4-(2-chloro-phenyl)-4-methyl-piperidine (0.59 g, 1.95 mmol) in 1,2-dichloroethane (10 mL) was treated with 1-chloroethyl chloroformate (0.28 mL, 2.6 mmol). This mixture was stirred for 12 hr at reflux, then evaporated in vacuo. The residue was redissolved in methanol (10 mL) and heated to reflux for 1 hr, then evaporated in vacuo. The resulting brown solid (the hydrochloric salt) was washed with ethyl acetate, then freebased with ethyl acetate/sodium hydroxide to yield 0.30 g (72%) of the title compound, ESI-MS m/z: 246 [M+1].

Workup

  1. temperatureat reflux
  2. customevaporated in vacuo
  3. dissolutionThe residue was redissolved in methanol (10 mL)
  4. temperatureheated
  5. temperatureto reflux for 1 hr
  6. customevaporated in vacuo
  7. washThe resulting brown solid (the hydrochloric salt) was washed with ethyl acetate

Sources & evidence

ORD record
ord-a073c4344ab843f69cdfb4ed56986d72
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

Loading…