1-Chloroethyl chloroformate → Hydrochloric Acid

HRID 584088Notes

Reaction equation

HRID 584088 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:25]C(OC(Cl)C)=O>ClCCCl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:15][C:16]=1[C:21]([F:24])([F:22])[F:23].[ClH:25]

Participants

5

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 223451981-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-piperidine

Product 2

HCID 313Hydrochloric AcidYield 882.2%HCID 166793174-[4-Chloro-3-(trifluoromethyl)phenyl]piperidine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 1-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-piperidine (1.1 g) in 1,2-dichloroethane (50 ml) was cooled to 0° C. Then α-chloroethyl chloroformate (1.5 g) dissolved in 1,2-dichloroethane (30 ml) was added dropwise at 0° C. The reaction mixture was then brought to reflux for 2 days. The volatiles were evaporated in vacuo and the residue triturated with methanol. The mixture was brought to reflux for 4 hours. The solvent was evaporated to afford the title compound as HCl salt (light brown crystals, 1.0 g) MS m/z (relative intensity, 70 eV) 263 (M+, 34), 262 (22), 83 (22), 57 (60), 56 (bp).

Workup

  1. additionwas added dropwise at 0° C
  2. temperatureto reflux for 2 days
  3. customThe volatiles were evaporated in vacuo
  4. customthe residue triturated with methanol
  5. temperatureto reflux for 4 hours
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-957a1502a8534bd9baf41e9e2a5b0198
Source dataset
uspto-grants-2005_08
Patent number
US06924374B2

Reaction notes

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