1-Chloroethyl chloroformate → HCID 69677716, compound

HRID 584175Notes

Reaction equation

HRID 584175 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)[C@H:10]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([CH3:32])[CH:26]=2)[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCl>[ClH:21].[Cl:22][C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([Cl:21])[CH:18]=1)[C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([CH3:32])[CH:26]=1)=[O:23]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 69677706HCID 69677706, compound

Product 1

HCID 69677716HCID 69677716, compoundYield 217.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-4-benzyl-1-(3,5-dichlorobenzoyl)-2-(3,4-dimethylbenzyl)piperazine (5.03 g) in dichloromethane (50 ml) was added 1-chloroethyl chloroformate (1.51 ml) slowly at 0° C., and then the mixture was heated at reflux under stirring. After 5.5 hours, the solvent was removed in vacuo and then the resulting residue was dissolved in methanol (20 ml) and refluxed for 0.5 hour. After removal of the solvent, the resulting residue was triturated with isopropyl ether to afford (2R)-1(3,5-dichlorobenzoyl)-2-(3,4-dimethylbenzyl)piperazine hydrochloride (4.84 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. customthe solvent was removed in vacuo
  4. dissolutionthe resulting residue was dissolved in methanol (20 ml)
  5. temperaturerefluxed for 0.5 hour
  6. customAfter removal of the solvent
  7. customthe resulting residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-6a82baf05c0844b6a3ce67734248910a
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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