Ammonium Hydroxide → HCID 12298167, compound

HRID 1448273Notes

Reaction equation

HRID 1448273 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]C)(=[O:4])[CH2:2][CH3:3].[C:10]1([NH:16][C:17]2([C:30]([O:32][CH2:33][CH2:34][CH3:35])=[O:31])[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-:36].[NH4+]>>[C:6]([OH:5])(=[O:9])[C:7]([OH:31])=[O:36].[CH2:33]([O:32][C:30]([C:17]1([N:16]([C:1](=[O:4])[CH2:2][CH3:3])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:18][CH2:19][N:20]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:21][CH2:22]1)=[O:31])[CH2:34][CH3:35]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 31263Propionic anhydrideHCID 12298152HCID 12298152, compound

Product 1

HCID 12298167HCID 12298167, compound

Procedure

260 parts of propanoic acid anhydride are added dropwise to 93 parts of propyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate while cooling in a water-bath. Upon completion, the whole is stirred and refluxed for 6 hours. After cooling, the reaction mixture is poured onto water, alkalized with ammonium hydroxide and the product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is dissolved in petroleumether. The solution is filtered and the filtrate is evaporated. The oily residue is converted into the ethanedioate salt in 2-propanone. The salt is filtered off and crystallized from a mixture of 2-propanone and ethanol (10:1 by volume), yielding propyl4-[N-(1-oxopropyl)-N-phenylamino]-1-(phenylmethyl)-4-piperidinecarboxylate ethanedioate; mp. 169.7° C.

Workup

  1. temperaturewhile cooling in a water-bath
  2. temperaturerefluxed for 6 hours
  3. temperatureAfter cooling
  4. additionthe reaction mixture is poured onto water
  5. extractionthe product is extracted with trichloromethane
  6. washThe extract is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. dissolutionThe residue is dissolved in petroleumether
  11. filtrationThe solution is filtered
  12. customthe filtrate is evaporated
  13. filtrationThe salt is filtered off
  14. customcrystallized from a mixture of 2-propanone and ethanol (10:1 by volume)

Sources & evidence

ORD record
ord-e63bc8855ed244b69b47bc82975b1eeb
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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