Sodium Carbonate → (+/-)5-{1-Hydroxy-2-[4-(2-pyridinyloxy)-1-piperidyl]ethyl}-3H-indol-2-one

HRID 1087046Notes

Reaction equation

HRID 1087046 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].C(=O)([O-])[O-].[Na+].[Na+].Cl.Cl.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.[BH4-].[K+]>O.C(O)C>[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:33]1[CH2:34][CH2:35][CH:30]([O:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)[CH2:31][CH2:32]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-oneHCID 4192641Potassium borohydrideHCID 146741542-(Piperidin-4-yloxy)pyridine dihydrochloride

Product 1

HCID 14678959(+/-)5-{1-Hydroxy-2-[4-(2-pyridinyloxy)-1-piperidyl]ethyl}-3H-indol-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 4.19 g (20 mmoles) 5-chloroacetyl-3H-indol-2-one, 150 ml ethanol, 6 g sodium carbonate and 5 g 4-(2-pyridinyloxy)piperidine dihydrochloride is heated under reflux for 2 h 30 min. The mixture is cooled in an ice bath, 10 ml water and then 8 g potassium borohydride are added and stirring is continued at ambient temperature of1 h. 300 ml water are added, the mixture is extracted with ethyl acetate and the extract is evaporated and purified by chromatography on a silica column, eluting with a 96/4 mixture of dichloromethane/ methanol. After recrystallization in 2-propanol 1.88 g of pure compound are isolated.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 h 30 min
  3. temperatureThe mixture is cooled in an ice bath
  4. customis continued at ambient temperature of1 h
  5. extractionthe mixture is extracted with ethyl acetate
  6. customthe extract is evaporated
  7. custompurified by chromatography on a silica column
  8. washeluting with a 96/4 mixture of dichloromethane/ methanol
  9. customAfter recrystallization in 2-propanol 1.88 g of pure compound
  10. customare isolated

Sources & evidence

ORD record
ord-246f1156ea274ec596717748dae570c7
Source dataset
uspto-grants-1991_07
Patent number
US05034401

Reaction notes

Loading…