1-Chloroethyl chloroformate → 4-[(2S,5R)-2,5-Dimethylpiperazin-1-yl]-2-methylbenzonitrile
Reaction equation
C([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH3:23])[CH:16]=2)[C@@H:10]([CH3:24])[CH2:9]1)C1C=CC=CC=1.C(Cl)(=O)OC(Cl)C>ClC(Cl)C>[CH3:24][C@H:10]1[CH2:9][NH:8][C@H:13]([CH3:14])[CH2:12][N:11]1[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH3:23])[CH:16]=1Participants
4
Procedure
Into 50 ml of dichloroethane was dissolved 1.81 g of 4-[(2S,5R)-4-benzyl-2,5-dimethylpiperazin-1-yl]-2-methylbenzonitrile, and then 1.62 g of 1-chloroethyl chlorocarbonate was added thereto, followed by heating under refluxing overnight. After the reaction solution was concentrated, 50 ml of methanol was added thereto, followed by heating under refluxing overnight. After the reaction solution was concentrated, water was added thereto, followed by washing with ether. The aqueous phase was made basic with a 1M sodium hydroxide aqueous solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then solvent was removed by evaporation to obtain 1.11 g of the title compound.