Oxygen → 1,3-dihydro-3-hydroxy-1-(1-piperidinyl)-3-(4-pyridinyl methyl)-2H-indol-2-one

HRID 487543Notes

Reaction equation

HRID 487543 reaction equation
[N:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]([CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:8]2=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[O:26]=O>>[OH:26][C:9]1([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]1=[O:23]

Participants

4

Reactant 3

HCID 977OxygenHCID 24758Sodium hydrideHCID 233539641,3-dihydro-1-(piperidinyl)-3-(4-pyridinylmethyl)-2H-indol-2-one

Product 1

HCID 233539681,3-dihydro-3-hydroxy-1-(1-piperidinyl)-3-(4-pyridinyl methyl)-2H-indol-2-oneYield 25%

Procedure

1,3-dihydro-1-(1-piperidinyl)-3-(4-pyridinyl methyl)-2H-indol-2-one could be reacted with sodium hydride and oxygen as reported in Example 22. After column chromatography, the product was recrystallized from hexane-chloroform to give the product as a brown solid, m.p. 156°-158° C. in 25% yield. High Res. Mass Spec. Calcd. for C19H21N3O2 : 324.1712(M+H). Found: 324.1709.

Workup

  1. customAfter column chromatography, the product was recrystallized from hexane-chloroform

Sources & evidence

ORD record
ord-713a482c723649e69c5861795dc27f41
Source dataset
uspto-grants-1994_03
Patent number
US05296478

Reaction notes

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