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

HRID 329845Notes

Reaction equation

HRID 329845 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O: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:16])[CH2:12][C:13]([CH3:15])=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[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:41]([C:42]([O:44][CH3:45])=[O:43])=[C:40]([CH3:46])[NH:39][C:13]([CH3:15])=[C:12]1[C:11]([O:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:22][CH2:21]1)=[O:16]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 11740518Butanoic acid, 3-oxo-, 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl ester

Product 1

HCID 198712602-(4-Benzhydryl-1-piperazinyl)ethyl methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 31.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2,3-dichlorobenzaldehyde, 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-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 84°-88° C. (sintering). Yield 31.6%. IR(Nujol)cm-1 : 3320, 1730, 1690. NMR(CDCl3) δ: 2.28(6H, s, ##STR17## 3.58(3H,s,COOCH3), 4.15(2H,t,J=6,--COOCH2CH2 --), 4.19(1H,s,>N--CH<), 5.45(1H,s,C(4) --H), 5.61(1H,s,NH).

Sources & evidence

ORD record
ord-faebba8f99ae4dc5a65170070e382f43
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

Loading…