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

HRID 329877Notes

Reaction equation

HRID 329877 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([O:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:22][CH2:21]1)(=[O:15])[CH2:11][C:12]([CH3:14])=O.[NH2:39]/[C:40](/[CH3:46])=[CH:41]\[C:42]([O:44][CH3:45])=[O:43]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:41]([C:42]([O:44][CH3:45])=[O:43])=[C:40]([CH3:46])[NH:39][C:12]([CH3:14])=[C:11]2[C:10]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][N:23]([CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:24][CH2:25]2)=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 198712333-[4-(Diphenylmethyl)piperazin-1-yl]propyl 3-oxobutanoate

Product 1

HCID 198712403-(4-Benzhydryl-1-piperazinyl)propyl methyl 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of m-chlorobenzaldehyde, 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 4-(3-chlorophenyl)-2,6-dimethyl-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 colorless crystals, m.p. 169°-172° C. Yield 45.6%.

Sources & evidence

ORD record
ord-a890f4a43ba8486092370d7a7a6cf978
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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