Hydrochloric Acid → 2-(4-Benzhydryl-1-piperazinyl)ethyl methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate dihydrochloride monohydrate

HRID 329842Notes

Reaction equation

HRID 329842 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:40]/[C:41](/[CH3:47])=[CH:42]\[C:43]([O:45][CH3:46])=[O:44].[ClH:48]>C(O)(C)C>[OH2:2].[ClH:48].[ClH:48].[CH3:16][C:14]1[NH:40][C:41]([CH3:47])=[C:42]([C:43]([O:45][CH3:46])=[O:44])[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[C:13]=1[C:12]([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH:27]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:23][CH2:22]1)=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 11740518Butanoic acid, 3-oxo-, 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl ester

Product 1

HCID 198712412-(4-Benzhydryl-1-piperazinyl)ethyl methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate dihydrochloride monohydrateYield 11.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of o-nitrobenzaldehyde, 2-(4-benzhydryl-1-piperazinyl)ethyl acetoacetate and methyl 3-aminocrotonate was worked up in isopropyl alcohol in the same manner as Example 1 and the product was further treated with methanolic hydrogen chloride to give 2-(4-benzhydryl-1-piperazinyl)ethyl methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate dihydrochloride monohydrate as light yellow crystals, m.p. 162°-164° C. Yield 11.4%.

Sources & evidence

ORD record
ord-7dfd042f3e564ba7989f1b318ce86a4b
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

Loading…