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

HRID 1088382Notes

Reaction equation

HRID 1088382 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a8c87f20404f400983afad13b9e94d2b
Source dataset
uspto-grants-1990_10
Patent number
US04962115

Reaction notes

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