Ammonium Hydroxide → HCID 12298217, compound

HRID 1973781Notes

Reaction equation

HRID 1973781 reaction equation
[C:1]1([NH:7][C:8]2([CH2:21][O:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]([O:30][C:31](=[O:34])[CH2:32]C)(=[O:29])[CH2:27][CH3:28].[OH-:35].[NH4+]>>[C:31]([OH:30])(=[O:34])[C:32]([OH:22])=[O:35].[C:1]1([N:7]([C:8]2([CH2:21][O:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[C:26](=[O:29])[CH2:27][CH3:28])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 31263Propionic anhydrideHCID 12298208HCID 12298208, compound

Product 1

HCID 12298217HCID 12298217, compound

Procedure

A mixture of 13.1 parts of N-phenyl-1-(phenylmethyl)-4-(propoxymethyl)-4-piperidinamine and 20 parts of propionic acid anhydride is stirred and refluxed for 6 hours. After cooling, the reaction mixture is poured onto ice-water and the whole is alkalized with ammonium hydroxide. The product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The oily residue is converted into the ethanedioate salt in 2-propanone and 2-propanol. The salt is filtered off and crystallized from acetonitrile, yielding N-phenyl-N-[1-(phenylmethyl)-4-(propoxymethyl)-4-piperidinyl]propanamide ethanedioate; mp. 180.3° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureAfter cooling
  3. additionthe reaction mixture is poured onto ice-water
  4. extractionThe product is extracted with trichloromethane
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. filtrationThe salt is filtered off
  10. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-7ba9983680074125896231ad9cc8e5b3
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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