3-Nitrobenzaldehyde → 2-(4-Benzyl-1-piperazinyl)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 329859Notes

Reaction equation

HRID 329859 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]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:34]/[C:35](/[CH3:41])=[CH:36]\[C:37]([O:39][CH3:40])=[O:38]>C(O)(C)C>[CH3:16][C:14]1[NH:34][C:35]([CH3:41])=[C:36]([C:37]([O:39][CH3:40])=[O:38])[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]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)=[O:17]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 198712152-(4-Benzylpiperazin-1-yl)ethyl 3-oxobutanoate

Product 1

HCID 198712002-(4-Benzyl-1-piperazinyl)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of m-nitrobenzaldehyde, 2-(4-benzyl-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-benzyl-1-piperazinyl)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 106°-108° C. (sintering). Yield 86.0%. IR(Nujol)cm-1 : 3325. NMR(CDCl3) δ: 2.33(6H,s, ##STR33## 3.46(2H,s,C6H5CH2 --), 3.61(3H,s,COOCH3), 4.14(2H,t,J=6,--COOCH2CH2 --), 5.09(1H,s,C(4) --H), 5.82(1H,s,NH).

Sources & evidence

ORD record
ord-7fa76f2a96de45bcbca964023b673864
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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