Isopropanol → HCID 19871207, compound

HRID 329848Notes

Reaction equation

HRID 329848 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:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13]C(C)=O.[NH2:42]/[C:43](/[CH3:49])=[CH:44]\[C:45]([O:47][CH3:48])=[O:46].[CH:50](O)(C)[CH3:51]>>[CH3:50][C:51]1[NH:42][C:43]([CH3:49])=[C:44]([C:45]([O:47][CH3:48])=[O:46])[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[CH2:22][CH2:23][N:24]([CH:27]([C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[CH2:25][CH2:26]1)=[O:17]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 19871204HCID 19871204, compound

Product 1

HCID 19871207HCID 19871207, compoundYield 53.1%

Procedure

A mixture of m-nitrobenzaldehyde, 2-[4-(4,4'-dimethylbenzhydryl)-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-(4,4'-dimethylbenzhydryl)-1-piperazinyl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 83°-87° C. (sintering). Yield 53.1%. IR(Nujol)cm-1 : 3330, 1695, 1680(shoulder). NMR(CDCl3) δ: 2.32(6H,s, ##STR19## 2.36(6H,s, ##STR20## 3.60(3H,s,COOCH3), 4.10(1H,s,>N--CH<), 4.14(2H,t,J=6, --COOCH2CH2 --), 5.09(1H,s,C(4) --H), 5.84(1H,broad s, NH).

Sources & evidence

ORD record
ord-254f96347eae4c018d4b2d7809f62717
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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