HCID 5851, compound → HCID 66735391, compound

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.C(O)(=O)[C@@H](C(C(O)=O)O)O.C([O-])(=O)C(C(C([O-])=O)O)O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]2[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 5851HCID 5851, compound

HCID 38061142,3-Dihydroxybutanedioate

HCID 66735189HCID 66735189, compound

Product 1

HCID 66735391HCID 66735391, compoundYield 6.3%

Procedure

According to the process disclosed in GB Patent No. 2 225 321, racemic 1-(4-chlorophenyl)-phenylmethyl-piperazine is resolved using 2 molar equivalent amount of (R)-tartaric acid and the tartarate salt having unsatisfactory optical purity obtained after three recrystallizations was neutralized. The thus obtained base was crystallized three times from hexane. The process provided (R)-(−)-1-(4-chlorophenyl)-phenylmethyl-piperazine in the yield of 6.3%. This method is not suitable for the use in the pharmaceutical industry since neither the product purity nor the yield are satisfactory.