Hydrochloric Acid → HCID 19045477、化合物

HRID 1781428ノート

反応式

HRID 1781428 の反応式
N1CCCC1.[OH:6][C:7]1[C:8]([C:16](=[O:18])[CH3:17])=[CH:9][C:10]2[O:14][CH2:13][O:12][C:11]=2[CH:15]=1.[C:19]1([CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[ClH:34]>CO.C(O)C>[ClH:34].[C:19]1([CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][C:30]3([CH2:17][C:16](=[O:18])[C:8]4[CH:9]=[C:10]5[O:14][CH2:13][O:12][C:11]5=[CH:15][C:7]=4[O:6]3)[CH2:29][CH2:28]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 96437N-Phenethyl-4-piperidinoneHCID 11745219Ethanone, 1-(6-hydroxy-1,3-benzodioxol-5-yl)-

生成物 1

HCID 19045477HCID 19045477、化合物収率 38%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 887Methanol溶媒2 回

実験手順

Pyrrolidine (83 ml, 71 mg, 1 mmol) was added to a mixture of 1-(6-hydroxy-1,3-benzodioxol-5-yl)-ethanone [prepared as described by K. Fukui and M. Nakayama, Bull. Chem: Soc. Jap., 1963, 37, 300.] (180 mg, 1 mmol) in methanol (1 ml). The mixture was stirred for 10 minutes, then 1-(2-phenylethyl)-4-piperidinone (203 mg, 1 mmol) in methanol (1 ml) was added and the mixture was heated under reflux for 1.5 hours. The mixture was cooled, the solvent was evaporated under reduced pressure and aqueous sodium hydrogen carbonate (saturated, 20 ml) was added. The mixture was extracted with dichloromethane (3×20 ml) and the combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with CH2Cl2 /MeOH/NH3 (Aq.) (98:2:0.2) to give a yellow glass which was suspended in ethanol (5 ml) and treated with ethanolic HCl (6N, 0.5 ml). The mixture was stirred for 1 hour, cooled and the precipitate was collected and dried in vacuo to give the title compound as a white solid (153 mg, 38%), m.p.>285° C.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure and aqueous sodium hydrogen carbonate (saturated, 20 ml)
  5. additionwas added
  6. extractionThe mixture was extracted with dichloromethane (3×20 ml)
  7. dry with materialthe combined organic fractions were dried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with CH2Cl2 /MeOH/NH3 (Aq.) (98:2:0.2)
  11. customto give a yellow glass which
  12. stirringThe mixture was stirred for 1 hour
  13. temperaturecooled
  14. customthe precipitate was collected
  15. customdried in vacuo

出典と根拠

ORDレコード
ord-4ffa9ca4431d46dc85f632b388fbb1f5
出典データセット
uspto-grants-1997_05
特許番号
US05633247

反応ノート

読み込み中…