Adipic Acid → Ivabradine adipate

HRID 523523Notes

Reaction equation

HRID 523523 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].C(O)C.[CH3:14][N:15]([CH2:35][C@@H:36]1[C:39]2[CH:40]=[C:41]([O:46][CH3:47])[C:42]([O:44][CH3:45])=[CH:43][C:38]=2[CH2:37]1)[CH2:16][CH2:17][CH2:18][N:19]1[C:29](=[O:30])[CH2:28][C:27]2[C:22](=[CH:23][C:24]([O:33][CH3:34])=[C:25]([O:31][CH3:32])[CH:26]=2)[CH2:21][CH2:20]1>ClCCl>[CH3:14][N:15]([CH2:35][C@@H:36]1[C:39]2[CH:40]=[C:41]([O:46][CH3:47])[C:42]([O:44][CH3:45])=[CH:43][C:38]=2[CH2:37]1)[CH2:16][CH2:17][CH2:18][N:19]1[C:29](=[O:30])[CH2:28][C:27]2[C:22](=[CH:23][C:24]([O:33][CH3:34])=[C:25]([O:31][CH3:32])[CH:26]=2)[CH2:21][CH2:20]1.[C:1]([O-:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 196Adipic AcidHCID 702EthanolHCID 132999Ivabradine

Product 1

HCID 86680271Ivabradine adipate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ivabradine adipate can be obtained by adding adipic acid, e.g. about one equivalent, in a suitable solvent, such as ethanol, to a solution of ivabradine in a suitable solvent, such as dichloromethane. Crystalline ivabradine adipate product can be obtained by removal of the solvent, e.g. under vacuum at about 40° C. Crystalline ivabradine adipate can also be obtained by adding a solution of adipic acid in water to a solution of ivabradine in ethanol, and removal of the solvent.

Sources & evidence

ORD record
ord-2c28ce3fbfbd4d39935e584c176d94bf
Source dataset
uspto-grants-2016_05
Patent number
US09339550B2

Reaction notes

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