Benzenesulfonic Acid → Amlodipine besylate

HRID 1761251Notes

Reaction equation

HRID 1761251 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[C@H:11]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].C([O-])(=O)[C@@H]([C@H](C([O-])=O)O)O.[C:39]1([S:45]([OH:48])(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(O)(C)C.O>[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[CH:42]1[CH:41]=[CH:40][C:39]([S:45]([OH:48])(=[O:47])=[O:46])=[CH:44][CH:43]=1

Participants

6

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 119400TartrateHCID 9801597(+)-Amlodipine

Product 1

HCID 60496Amlodipine besylateYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

68.8 gm (0.122 mole, 95.2% de) R (+) amlodipine hemi L(+) tartarate mono DMSO solvate prepared as per example-2 was suspended in aqueous isopropanol (70 ml IPA: 250 ml distilled water) and a solution of benzene sulfonic acid (21.28 gm of 90% technical grade, 0.122 mole) in 1150 ml water was added. The reaction mixture was stirred for 2 hrs and the slurry was filtered, washed with distilled water, hexane, the solid was dried under vac. at 40° C. till constant weight to give R(+) amlodipine besylate (66.74 gm, 89.1% yield) 98.7 ee by chiral HPLC.

Workup

  1. filtrationthe slurry was filtered
  2. washwashed with distilled water, hexane
  3. customthe solid was dried under vac

Sources & evidence

ORD record
ord-4a82a11c70c04711a8b6114af30acf83
Source dataset
uspto-grants-2005_01
Patent number
US06846932B1

Reaction notes

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