1-Chloroethyl chloroformate → trans-4-(2,5-Dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile

HRID 1838241Notes

Reaction equation

HRID 1838241 reaction equation
ClC(OC(Cl)C)=O.C([N:15]1[C@H:20]([CH3:21])[CH2:19][N:18]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=2)[C@@H:17]([CH3:34])[CH2:16]1)C1C=CC=CC=1>ClC(Cl)C>[CH3:34][C@H:17]1[CH2:16][NH:15][C@H:20]([CH3:21])[CH2:19][N:18]1[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 11639373(2S,5R)-4-(4-Benzyl-2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile

Product 1

HCID 11391932trans-4-(2,5-Dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrileYield 80.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A 0.92 ml portion of 1-chloroethyl chloroformate was added to 20 ml of dichloroethane solution containing 0.31 g of (2S,5R)-4-(4-benzyl-2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile, and the mixture was stirred for 2 days with heating under reflux. The reaction mixture was concentrated, mixed with 20 ml of methanol and then stirred for 1 day with heating under reflux. The reaction mixture was concentrated and the residue was subjected to a silica gel column chromatography and purified with chloroform-methanol (9:1, v/v) to obtain 0.19 g of the title compound as a yellow oil.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. additionmixed with 20 ml of methanol
  5. stirringstirred for 1 day
  6. temperaturewith heating
  7. temperatureunder reflux
  8. concentrationThe reaction mixture was concentrated
  9. custompurified with chloroform-methanol (9:1

Sources & evidence

ORD record
ord-2342bc2303f14deea84f2751770ce840
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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