Reaction equation
CC1NC(C)=C(C(OC)=O)C([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=2)C=1C([O:10][CH2:11][CH2:12][N:13]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:14])=O.CC1NC(C)=C(C(OC)=O)C([C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([N+:53]([O-])=O)[CH:48]=2)C=1C(OC)=O.[CH3:61]OC(C1C(C2C=CC=C([N+]([O-])=O)C=2)C(C(O)=O)=C(C)NC=1C)=O>>[OH:10][CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH:49]1([N:53]=[C:61]=[N:28][CH:24]2[CH2:23][CH2:22][CH2:27][CH2:26][CH2:25]2)[CH2:48][CH2:47][CH2:52][CH2:51][CH2:50]1Participants
Procedure
A new, technologically easily feasible process for the preparation of 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, comprising a partrial hydrolysis of dimethyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate in an inert organic solvent at a temperature between room temperature and the reflux temperature of the reaction mixture with an aqueous solution of alkali hydroxide and the reaction of the obtained 3-methoxycarbonyl-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid either with N-(2-hydroxyethyl)-N-benzyl-methylamine in the presence or absence of an organic solvent in the presence of N,N'-dicyclohexylcarbodiimide at a temperature of between 25° and 120° C. or with N-(2-haloethyl)-N-benzyl-methylamine in the presence of an inert organic solvent and of a proton acceptor at a temperature of between 25° and 140° C., to yield the title compound, which can be, if desired, converted to its hydrochloride salt. The hydrochloride salt is known under the generic name "nicardipine hydrochloride" and is used as a valuable therapeutic in the therapy of cerebral insufficiency.
Sources & evidence
- ORD record
- ord-1aa175d88ccb48f6af997dc90c9def8b
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04769465
Linked notes
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