Ammonium Hydroxide → HCID 12298217, compound

HRID 1448279Notes

Reaction equation

HRID 1448279 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-5899de588f4044aa8f75938de1391467
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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