Isopropanol → HCID 19871249, compound

HRID 329870Notes

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](/[CH3:50])=[CH:44]\[C:45]([O:47][CH2:48][CH3:49])=[O:46].[CH:51](O)(C)[CH3:52]>>[CH3:51][C:52]1[NH:42][C:43]([CH3:50])=[C:44]([C:45]([O:47][CH2:48][CH3:49])=[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[CH2:26][CH2:25][N:24]([CH:27]([C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)[C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=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 19871204HCID 19871204, compound

Product 1

HCID 19871249HCID 19871249, compoundYield 50.8%

Procedure

A mixture of m-nitrobenzaldehyde, 2-[4-(4,4'-dimethylbenzhydryl)-1-piperazinyl]ethyl acetoacetate and ethyl 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 ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 82°-85° C. (sintering). Yield 50.8%. IR(Nujol)cm-1 : 3330, 1685. NMR(CDCl3) δ: 1.19(3H,t,J=7,--CH2CH3), 2.26(6H,s, ##STR40## 2.33(6H,s, ##STR41## 4.05(2H,q,J=7,--CH2CH3), 4.10(1H,s,>N--CH<), 4.12(2H,t,J=6,--COOCH2CH2 --), 5.07(1H,s,C(4) --H), 5.75(1H, broad s, NH).

Sources & evidence

ORD record: ord-19b2815bf99e4c0c87ff59ada4419f9f
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04892875

Reaction notes

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