2-Pyridone → 3-(3-Chlorophenyl)-5-(4-chlorophenyl)-1-methylpiperidin-4-one

HRID 462015Notes

Reaction equation

HRID 462015 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](=[O:14])[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[CH:11][N:10]([CH3:22])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CC(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13](=[O:14])[CH:12]([C:15]3[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=3)[CH2:11][N:10]([CH3:22])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 88712-PyridoneHCID 128792353-(3-Chlorophenyl)-5-(4-chlorophenyl)-1-methylpyridin-4(1H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 203170023-(3-Chlorophenyl)-5-(4-chlorophenyl)-1-methylpiperidin-4-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 10 g. portion of 3-(3-chlorophenyl)-5-(4-chlorophenyl)-1-methyl-4(1H)-pyridinone was made from 33.6 g. of the corresponding 2-propanone by the procedures of Examples 1-3. The pyridinone was reduced with lithium aluminum hydride and the reaction mixture was separated by chromatography as described in the examples above. The products of Examples 15 and 16 were obtained as a mixture containing both, combined yield 2.1 g., m.p. 125.5°.

Workup

  1. customthe reaction mixture was separated by chromatography

Sources & evidence

ORD record
ord-558f29a58adc4b258d6bd1bcf92e38c8
Source dataset
uspto-grants-1977_12
Patent number
US04065290

Reaction notes

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