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

HRID 329841Notes

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][N:21]1[CH2:26][CH2:25][N:24]([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13]C(C)=O.[NH2:40]/[C:41](/[CH3:48])=[CH:42]\[C:43]([O:45][CH2:46][CH3:47])=[O:44].[CH:49](O)(C)[CH3:50]>>[CH3:49][C:50]1[NH:40][C:41]([CH3:48])=[C:42]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[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][N:21]1[CH2:26][CH2:25][N:24]([CH:27]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)=[O:17]

Participants

Reactant 4

HCID 3776Isopropanol

HCID 74493-Nitrobenzaldehyde

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

HCID 11740518Butanoic acid, 3-oxo-, 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl ester

Product 1

HCID 198712662-(4-Benzhydryl-1-piperazinyl)ethyl ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 48.3%

Procedure

A mixture of m-nitrobenzaldehyde, 2-(4-benzhydryl-1-piperazinyl)ethyl acetoacetate and ethyl 3-aminocrotonate was reacted in isopropyl alcohol in the same manner as Example 1 to give 2-(4-benzhydryl-1-piperazinyl)ethyl ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 80°-82° C. (sintering). Yield 48.3%. IR(Nujol)cm-1 : 3320, 1695, 1680. NMR(CDCl3) δ: 1.18(3H,t,J=6,--CH2CH3), 2.33(6H,s, ##STR14## 4.08(2H,q,J=6, --CH2CH3), 4.15(2H,t,J=6, --COOCH2CH2 --), 4.18(1H,s,>N--CH<), 5.08(1H,s,C(4) --H), 5.79(1H,s,NH).

Sources & evidence

ORD record: ord-95d69f90a2884464bdb1d6f0f2247631
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04892875

Reaction notes

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