Potassium Hydroxide → cis-3-methoxy-N,N-bis(phenylmethyl)-4-piperidinamine

HRID 1110391노트

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HRID 1110391 반응식
[OH-].[K+].[C:3]1([CH2:9][N:10]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:11]2[CH2:16][CH2:15][N:14](C(OCC)=O)[CH2:13][C@H:12]2[O:22][CH3:23])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CC(O)C>[CH3:23][O:22][C@H:12]1[C@@H:11]([N:10]([CH2:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:16][CH2:15][NH:14][CH2:13]1

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 67922776HCID 67922776, 화합물

생성물 1

HCID 67922653cis-3-methoxy-N,N-bis(phenylmethyl)-4-piperidinamine수율 55%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a stirred mixture of 230 parts of potassium hydroxide and 1600 parts of 2-propanol were added 155 parts of ethyl cis-4-[bis(phenylmethyl)amino]-3-methoxy-1-piperidinecarboxylate. The whole was stirred and refluxed for 7 hours. The reaction mixture was evaporated. Water was added and the mixture was evaporated till all traces of 2-propanol were removed. The product was extracted with dichloromethane. The extract was washed twice with a sodium chloride solution in water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was taken up in dichloromethane. The solution was washed with a sodium hydroxide solution 5%, dried, filtered and evaporated, yielding 70 parts (55%) of cis-3-methoxy-N,N-bis(phenylmethyl)-4-piperidinamine as a residue (int. 47).

후처리

  1. temperaturerefluxed for 7 hours
  2. customThe reaction mixture was evaporated
  3. additionWater was added
  4. customthe mixture was evaporated till all traces of 2-propanol
  5. customwere removed
  6. extractionThe product was extracted with dichloromethane
  7. washThe extract was washed twice with a sodium chloride solution in water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol
  13. customThe pure fractions were collected
  14. customthe eluent was evaporated
  15. washThe solution was washed with a sodium hydroxide solution 5%
  16. customdried
  17. filtrationfiltered
  18. customevaporated

출처 및 근거

ORD 기록
ord-affa86943f864cfb8c6eb69899aa20f1
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04975439

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