Hydrochloric Acid → (+)-cis-3-methoxy-N-(1-phenylethyl)-4-piperidinamine

HRID 345577노트

반응식

HRID 345577 반응식
[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[CH2:7][CH2:6][N:5](C(OCC)=O)[CH2:4]1.Cl>>[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[CH2:7][CH2:6][NH:5][CH2:4]1

참가 물질

3

반응물 2

HCID 313Hydrochloric AcidHCID 67914576(+)-Ethyl cis-3-methoxy-4-[(1-phenylethyl)amino]-1-piperidinecarboxylate

생성물 1

HCID 67914506(+)-cis-3-methoxy-N-(1-phenylethyl)-4-piperidinamine수율 100%

실험 절차

A solution of 16 parts of (+)-ethyl cis-3-methoxy-4-[(1-phenylethyl)amino]-1-piperidinecarboxylate in 170 parts of a hydrochloric acid solution 6N was stirred and refluxed for 45 hours. The reaction mixture was cooled and washed with dichloromethane. The aqueous phase was cooled in an ice-bath and treated with ammonium hydroxide. The product was extracted three times with 130 parts of dichloromethane. The combined extracts were washed with 10 parts of water, dried, filtered and evaporated. The residue was dissolved in methylbenzene and the latter was evaporated again, yielding 12.2 parts (100%) of (+)-cis-3-methoxy-N-(1-phenylethyl)-4-piperidinamine as a residue (intermediate 105).

후처리

  1. temperaturerefluxed for 45 hours
  2. temperatureThe reaction mixture was cooled
  3. washwashed with dichloromethane
  4. temperatureThe aqueous phase was cooled in an ice-bath
  5. additiontreated with ammonium hydroxide
  6. extractionThe product was extracted three times with 130 parts of dichloromethane
  7. washThe combined extracts were washed with 10 parts of water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. dissolutionThe residue was dissolved in methylbenzene
  12. customthe latter was evaporated again

출처 및 근거

ORD 기록
ord-1d4483c24d8346c4b2c70aefb4ba4130
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05057525

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