Isopropanol → HCID 19871231, compound

HRID 329847Notes

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]([F:41])=[CH:37][CH:36]=2)[C:28]2[CH:33]=[CH:32][C:31]([F: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:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:25][CH2:26]1)=[O:17]

Participants

Reactant 4

HCID 3776Isopropanol

HCID 74493-Nitrobenzaldehyde

HCID 643918Methyl 3-aminocrotonate

HCID 19871201HCID 19871201, compound

Product 1

HCID 19871231HCID 19871231, compoundYield 33.3%

Procedure

A mixture of m-nitrobenzaldehyde, 2-[4-(4,4'-difluorobenzhydryl)-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'-difluorobenzhydryl)-1-piperazinyl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 68°-72° C. (sintering). Yield 33.3%. This product was treated with methanolic hydrogen chloride to give colorless prisms of the dihydrochloride, m.p. 190°-193° C.

Sources & evidence

ORD record: ord-617ab15aab76475ea097460b20ca7200
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04892875

Reaction notes

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