Ethanol → (+/-)5-[1-Hydroxy-2-(4-phenoxy-1-piperidyl)ethyl]-3H-indol-2-one

HRID 1087043Notes

Reaction equation

HRID 1087043 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)=[O:4].Cl.[O:16]([CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)C.[BH4-].[K+]>O>[OH:4][CH:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)[CH2:2][N:26]1[CH2:27][CH2:28][CH:23]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 702EthanolHCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-oneHCID 4192641Potassium borohydrideHCID 177497864-Phenoxypiperidine hydrochloride

Product 1

HCID 14580203(+/-)5-[1-Hydroxy-2-(4-phenoxy-1-piperidyl)ethyl]-3H-indol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4.19 g (20 mmoles) 5-chloroacetyl-3H-indol-2-one 4 g dry sodium carbonate, 4.27 g (20 mmoles) 4-phenoxypiperidine hydrochloride and 100 ml ethanol is heated under reflux fo 1 h 15 min under an argon atmosphere. The mixture is left to cool, 10 ml water, then 8 g potassium borohydride are added and stirring is continued for 2 h 30 min at ambient temperature. A further 200 ml water are added, the mixture is stirred for 30 min and filtered, and the solid is washed with water and dried. 4.67 g of oohre orystals are obtained, which are purified by chromatography on a silica column, eluting with a 95/5 mixture of dichloromethane/ methanol.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. waitThe mixture is left
  4. temperatureto cool
  5. waitis continued for 2 h 30 min at ambient temperature
  6. stirringthe mixture is stirred for 30 min
  7. filtrationfiltered
  8. washthe solid is washed with water
  9. customdried
  10. custom4.67 g of oohre orystals are obtained
  11. customwhich are purified by chromatography on a silica column
  12. washeluting with a 95/5 mixture of dichloromethane/ methanol

Sources & evidence

ORD record
ord-5a71746f00c4446fbfd6caa1a7cea8b2
Source dataset
uspto-grants-1991_07
Patent number
US05034401

Reaction notes

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