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

HRID 329861Notes

Reaction equation

HRID 329861 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][N:19]1[CH2:24][CH2:23][N:22]([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][CH2:20]1)(=[O:15])[CH2:11][C:12]([CH3:14])=O.[NH2:38]/[C:39](/[CH3:45])=[CH:40]\[C:41]([O:43][CH3:44])=[O:42]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:40]([C:41]([O:43][CH3:44])=[O:42])=[C:39]([CH3:45])[NH:38][C:12]([CH3:14])=[C:11]2[C:10]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([CH:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:21][CH2:20]2)=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 11740518Butanoic acid, 3-oxo-, 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl ester

Product 1

HCID 198712632-(4-Benzhydryl-1-piperazinyl)ethyl methyl 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 28.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of m-chlorobenzaldehyde, 2-(4-benzhydryl-1-piperazinyl)ethyl acetoacetate and methyl 3-aminocrotonate was worked up in isopropyl alcohol in the same manner as Example 1 to give 2-(4-benzhydryl-1-piperazinyl)ethyl methyl 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 74°-80° C. (sintering). Yield 28.3%. IR(Nujol)cm-1 : 3325, 1695, 1680. NMR(CDCl3) δ: 2.32(6H,s, ##STR36## 3.60(3H,s,COOCH3), 4.96(1H,s,C(4) --H), 5.64(1H,broad s, NH).

Sources & evidence

ORD record
ord-99bb6428d72442278e8c8e2a6eba242e
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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