Isopropanol → 3-(4-Benzhydryl-1-piperazinyl)propyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 329876Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH2:23]1)(=[O:17])[CH2:13]C(C)=O.[NH2:41]/[C:42](/[CH3:48])=[CH:43]\[C:44]([O:46][CH3:47])=[O:45].[CH:49](O)(C)[CH3:50]>>[CH3:49][C:50]1[NH:41][C:42]([CH3:48])=[C:43]([C:44]([O:46][CH3:47])=[O:45])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:13]=1[C:12]([O:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:26][CH2:27]1)=[O:17]

Participants

Reactant 4

HCID 3776Isopropanol

HCID 74493-Nitrobenzaldehyde

HCID 643918Methyl 3-aminocrotonate

HCID 198712333-[4-(Diphenylmethyl)piperazin-1-yl]propyl 3-oxobutanoate

Product 1

HCID 200686763-(4-Benzhydryl-1-piperazinyl)propyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Procedure

A mixture of m-nitrobenzaldehyde, 3-(4-benzhydryl-1-piperazinyl)propyl acetoacetate and methyl 3-aminocrotonate was worked up in isopropyl alcohol in the same manner as Example 1 to give 3-(4-benzhydryl-1-piperazinyl)propyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as an oil. This product was further treated with methanolic hydrogen chloride. Recrystallization from methanol gave the dihydrochloride as light yellow crystals, m.p. 168°-173° C. Yield 34.3%.

Sources & evidence

ORD record: ord-a85c85da651641e8871a3a3ef9fe92bb
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04892875

Reaction notes

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