4-Piperidone → HCID 21492266, compound

HRID 1578394Notes

Reaction equation

HRID 1578394 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[O:11]=[C:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>>[O:11]=[C:12]1[CH2:17][CH2:16][N:15]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 337214-PiperidoneHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 21492266HCID 21492266, compound

Procedure

Moreover, the 4-fluoro-phenyl-acetonitrile can be reacted with 4-oxo-piperidine, to yield the 4-(4-oxo-piperidino)-phenylacetonitrile, which is hydrolyzed to the free acid and the acid esterified, to yield corresponding ethyl esters. The carbonyl group therein is reduced with one equivalent of Grignard compounds, e.g. methyl-, ethyl- or n-propyl-magnesium bromide, to yield the ethyl 4-[4-hydroxy-4-(methyl, ethyl or n-propyl)-piperidino]-phenyl acetate. Analogously, the α-[3-chloro-4-(4-hydroxy-4-methyl-piperidino)-phenyl]-propionate is obtained.

Sources & evidence

ORD record
ord-774a4feb0a3b47b8828b4d928cb8207a
Source dataset
uspto-grants-1976_02
Patent number
US03936467

Reaction notes

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