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

HRID 557010Notes

Reaction equation

HRID 557010 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 hydrochloride 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 hydrochloride salt) was washed with ethyl acetate

Sources & evidence

ORD record
ord-04955d163fcf4e76bb17117f9e7e472a
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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