3-(Trifluoromethyl)benzaldehyde → HCID 19871258, compound

HRID 329862Notes

Reaction equation

HRID 329862 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.C(OC[CH2:21][N:22]1[CH2:27][CH2:26][N:25]([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)[CH2:24][CH2:23]1)(=O)CC(C)=O.[NH2:41]/[C:42](/[CH3:48])=[CH:43]\[C:44]([O:46][CH3:47])=[O:45]>C(O)(C)C>[CH3:48][C:42]1[NH:41][C:42]([CH3:48])=[C:43]([C:44]([O:46][CH3:47])=[O:45])[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:12])([F:11])[F:1])[CH:4]=2)[C:43]=1[C:44]([O:46][CH2:47][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([CH:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:24][CH2:23]1)=[O:45]

Participants

5

Reactant 3

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 11740518Butanoic acid, 3-oxo-, 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl ester

Product 1

HCID 19871258HCID 19871258, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of m-trifluoromethylbenzaldehyde, 2-(4-benzhydryl-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-benzhydryl-1-piperazinyl)ethyl methyl 2,6-dimethyl-4-(3-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 70°-72° C. Yield 52.5%. The product was further treated with methanolic hydrogen chloride and recrystallized from methanolethyl ether to give the dihydrochloride as colorless crystals, m.p. 168°-170° C.

Sources & evidence

ORD record
ord-44b45d0e80f544f98d7c86c2d887217f
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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