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

HRID 329843Notes

Reaction equation

HRID 329843 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=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:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:40]([C:41]([O:43][CH3:44])=[O:42])=[C:39]([CH3:45])[NH:38][C:12]([CH3:14])=[C:11]1[C:10]([O:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:21][CH2:20]1)=[O:15]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 11740518Butanoic acid, 3-oxo-, 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl ester

Product 1

HCID 198712722-(4-Benzhydryl-1-piperazinyl)ethyl methyl 4-(2-chlorophenyl)-2,6-dimethyl--1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of o-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-(2-chlorophenyl)-2,6-dimethyl--1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 81°-83° C. (sintering). Yield (30.8%). IR(Nujol)cm-1 : 3320, 1680. NMR(CDCl3)δ: 2.26(6H,s, ##STR15## 3.56(3H,s,COOCH3), 4.12(2H,t,J=6,--COOCH2CH2 --), 4.17(1H,s, >N--CH<), 5.36(1H,s,C(4) --H), 5.63(1H,s,NH).

Sources & evidence

ORD record
ord-24035eb2b51b4134ae6368a02d1881ef
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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