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

HRID 1087046노트

반응식

HRID 1087046 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-246f1156ea274ec596717748dae570c7
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05034401

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