4-(4-Fluorobenzoyl)piperidine → HCID 70395401, compound

HRID 1721895Notes

Reaction equation

HRID 1721895 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]([C:7]1[CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=2[Cl:26])[C:9]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([CH3:14])[NH:11][C:12]=1[CH3:13])=[O:6].[F:27][C:28]1[CH:41]=[CH:40][C:31]([C:32]([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[O:33])=[CH:30][CH:29]=1>>[F:27][C:28]1[CH:29]=[CH:30][C:31]([C:32]([CH:34]2[CH2:39][CH2:38][N:37]([CH2:2][CH2:3][O:4][C:5]([C:7]3[CH:8]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=4[Cl:26])[C:9]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([CH3:14])[NH:11][C:12]=3[CH3:13])=[O:6])[CH2:36][CH2:35]2)=[O:33])=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 10549977HCID 10549977, compound

Product 1

HCID 70395401HCID 70395401, compound

Procedure

A mixture of 8.4 g of 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 2-chloroethyl ester and 8.8 g of 4-(p-fluorobenzoyl)-piperidine is stirred under argon for 1 hour at a temperature of 145°. After working up, the resulting residue is chromatographed over 500 g of silica gel, yielding 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 2-[4-(p-fluorobenzoyl)-piperidino]-ethyl ester in amorphous form which exhibits the following characteristic bands in th NMR spectrum: 1H-NMR (CDCl3): 2.3 and 2.4 [2S, 6H, 2 H3C--C (2 and 6)]; 3.6 [s, 3H, H3C--OOC]; 5.4 [s, 1H, H-c (4)], 7.1-8.1 (m, 7H, 7 arom. H). Rf value: 0.40 (hexane/ethyl acetate/methanol=4:2:1).

Workup

  1. customthe resulting residue is chromatographed over 500 g of silica gel

Sources & evidence

ORD record
ord-c1f3ac234ef146d4bcd7b56a864f98ee
Source dataset
uspto-grants-1989_08
Patent number
US04853393

Reaction notes

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