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

HRID 1087046ノート

反応式

HRID 1087046 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-246f1156ea274ec596717748dae570c7
出典データセット
uspto-grants-1991_07
特許番号
US05034401

反応ノート

読み込み中…