3-Chlorobenzaldehyde → HCID 19871239, compound

HRID 329878Notes

Reaction equation

HRID 329878 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([O:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)(=[O:15])[CH2:11][C:12]([CH3:14])=O.[NH2:32]/[C:33](/[CH3:39])=[CH:34]\[C:35]([O:37][CH3:38])=[O:36]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:34]([C:35]([O:37][CH3:38])=[O:36])=[C:33]([CH3:39])[NH:32][C:12]([CH3:14])=[C:11]2[C:10]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 153212052-[4-(4-Fluorophenyl)piperazin-1-yl]ethyl 3-oxobutanoate

Product 1

HCID 19871239HCID 19871239, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of m-chlorobenzaldehyde, 2-[4-(4-fluorophenyl)-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-fluorophenyl)-1-piperazinyl]ethyl methyl 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 44°-49° C. (sintering). Yield 34.1%. IR(Nujol)cm-1 : 3430, 1700, 1685. NMR(CDCl3) δ: 2.30(3H,s, ##STR58## 2.34(3H,s, ##STR59## 3.63(3H,s,--COOCH3), 4.18(2H,t,J=6,--COOCH2CH2 --), 4.99(1H,s,C(4) --H), 5.69(1H,s,NH).

Sources & evidence

ORD record
ord-c47cea4b51ce4c4eac17a7f003ad3011
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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