Hydrochloric Acid → HCID 19045477, 화합물

HRID 1591229노트

반응식

HRID 1591229 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 19045477HCID 19045477, 화합물수율 38%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-32b3e208f0ef4845ba3f7f7e91920ab6
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05206240

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