2-Pyridone → 3-(3-Bromophenyl)-1-methyl-5-phenyl-4-piperidinone

HRID 867038Notes

Reaction equation

HRID 867038 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](=[O:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][N:10]([CH3:21])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CC(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13](=[O:14])[CH:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][N:10]([CH3:21])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 88712-PyridoneHCID 128792753-(3-Bromophenyl)-1-methyl-5-phenylpyridin-4(1H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 203170063-(3-Bromophenyl)-1-methyl-5-phenyl-4-piperidinone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 10 g. portion of 3-(3-bromophenyl)-1-methyl-5-phenyl-4(1H)-pyridinone was made from 22 g. of the corresponding 2-propanone as described in Examples 1-3. The pyridinone was reduced with 2 g. of lithium aluminum hydride as described in the examples above, and the reaction mixture was chromatographed as described above with benzene-ethyl acetate mixtures. The combined yield of the compounds of Examples 13 and 13a was 4 g., molecular weight 341 by mass spectroscopy. The yield of the compound of Example 14 was 0.5 g., molecular weight by mass spectroscopy 343.

Workup

  1. customwas chromatographed

Sources & evidence

ORD record
ord-412b3a84a23b431991d4422393c54629
Source dataset
uspto-grants-1978_07
Patent number
US04102669

Reaction notes

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