HCID 5851, compound → HCID 66735391, compound

HRID 2263486Notes

Reaction equation

HRID 2263486 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

4

Reactant 3

HCID 5851HCID 5851, compoundHCID 38061142,3-DihydroxybutanedioateHCID 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.

Workup

  1. customobtained
  2. customafter three recrystallizations
  3. customThe thus obtained base was crystallized three times from hexane

Sources & evidence

ORD record
ord-0c5b67c592bd4e59b7821684f7165b0d
Source dataset
uspto-grants-2010_12
Patent number
US07851627B2

Reaction notes

Loading…