Potassium Hydroxide → HCID 67922653, compound

HRID 2248625Notes

Reaction equation

HRID 2248625 reaction equation
[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

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67922776HCID 67922776, compound

Product 1

HCID 67922653HCID 67922653, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred mixture of 230 parts of potassium hydroxide and 1600 parts of 2-propanol was 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).

Workup

  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

Sources & evidence

ORD record
ord-21f0e65c97214f16a06e2e1604c06cd5
Source dataset
uspto-grants-1991_08
Patent number
US05041454

Reaction notes

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