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

HRID 238288
Notes
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Reaction equation

HRID 238288 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.C(N1CCC(C2C=CC(Cl)=CC=2)(C)CC1)C1C=CC=CC=1.ClC(OC(Cl)=O)C.ClC1C=CC(C2(C)CCNCC2)=CC=1>CO>[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5213051-Chloroethyl chloroformateHCID 15469930HCID 15469930, compoundHCID 18675725HCID 18675725, compoundHCID 23136891HCID 23136891, compound

Product 1

HCID 231369824-(2-Chlorophenyl)-4-methylpiperidine

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

The mixture of 1-benzyl-4-(2-chloro-phenyl)-4-methylpiperidine and 1-benzyl-4-(4-chloro-phenyl)-4-methyl-piperidine (1.6 g) was dissolved in methanol (30 mL) and 1-chloroethylchloroformate (0.9 mL) was added. The mixture was heated at reflux for 10 minutes and allowed to cool. The solvent was removed by evaporation under vacuum and the residue precipitated from ethyl acetate with ether to give a 4:1 mixture of the title compound and 4-(4-chloro-phenyl)-4-methyl-piperidine which was used directly without further purification. LCMS m/z 210.2 [M+H]+. R.T.=2.64 min (Analytical Method 4).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 minutes
  3. temperatureto cool
  4. customThe solvent was removed by evaporation under vacuum
  5. customthe residue precipitated from ethyl acetate with ether
  6. customto give

Sources & evidence

ORD record
ord-4efed432bd794affafebc2c42892db68
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642621B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes