1-Chloroethyl chloroformate → HCID 86602694, compound

HRID 1374996Notes

Reaction equation

HRID 1374996 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[C@H:10]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([O:38][CH3:39])[CH:32]=2)[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[ClH:37].[F:27][C:25]([F:26])([F:28])[C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([C:21]([F:23])([F:24])[F:22])[CH:18]=1)[C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([O:38][CH3:39])[CH:32]=1)=[O:29]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 54051500HCID 54051500, compound

Product 1

HCID 86602694HCID 86602694, compoundYield 198%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(4-chloro-3-methoxybenzyl)piperazine (2.23 g) and 1-chloroethyl chloroformate (0.61 ml) in 1,2-dichloroethane (10 ml) was stirred under reflux for 15 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The resulting syrup was dissolved into methanol (10 ml) and the solution was stirred under reflux for 2 hours. After cooling, the reaction mixture was concentrated under reduced pressure and the resulting powder was collected by filtration to give a yellow powder of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(4-chloro-3-methoxybenzyl)piperazine hydrochloride (2.00 g).

Workup

  1. temperatureunder reflux for 15 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe resulting syrup was dissolved into methanol (10 ml)
  5. temperatureunder reflux for 2 hours
  6. temperatureAfter cooling
  7. concentrationthe reaction mixture was concentrated under reduced pressure
  8. filtrationthe resulting powder was collected by filtration

Sources & evidence

ORD record
ord-9a4d09d638524039884d4d5e1c8f71c8
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

Loading…