Isopropanol → HCID 19871234, compound

HRID 329854Notes

Reaction equation

HRID 329854 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[CH2:27][CH2:26][CH2:25][N:24]([CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13]C(C)=O.[NH2:41]/[C:42](/[CH3:48])=[CH:43]\[C:44]([O:46][CH3:47])=[O:45].[CH:49](O)(C)[CH3:50]>>[CH3:49][C:50]1[NH:41][C:42]([CH3:48])=[C:43]([C:44]([O:46][CH3:47])=[O:45])[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[CH2:27][CH2:26][CH2:25][N:24]([CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][CH2:22]1)=[O:17]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 19871257HCID 19871257, compound

Product 1

HCID 19871234HCID 19871234, compoundYield 31.7%

Procedure

A mixture of m-nitrobenzaldehyde, 2-(4-benzhydrylhomopiperazin-1-yl)ethyl acetoacetate and methyl 3-aminocrotonate was worked up in isopropyl alcohol in the same manner as Example 1 to give 2-(4-benzhydrylhomopiperazin-1-yl)-ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 60°-63° C. (sintering). Yield 31.7%. IR(KBr)cm-1 : 3330, 1690. NMR(CDCl3) δ: 2.33(6H,s, ##STR26## 3.60(3H,s), 4.12(2H,t,J=6), 4.57(1H,s,>N--CH<), 5.10(1H,s,C(4) --H), 5.92(1H,s,NH).

Sources & evidence

ORD record
ord-aacdef7b748b40198cab427f21661171
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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