Ammonium Hydroxide → N-(1-Benzyl-4-(methoxymethyl)-4-piperidyl)-N-phenylpropionamide oxalate

HRID 1448275Notes

Reaction equation

HRID 1448275 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5]1.[C:24]([O:28][C:29](=[O:32])[CH2:30]C)(=[O:27])[CH2:25][CH3:26].[OH-:33].[NH4+]>>[C:29]([OH:28])(=[O:32])[C:30]([OH:2])=[O:33].[CH3:1][O:2][CH2:3][C:4]1([N:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:24](=[O:27])[CH2:25][CH3:26])[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 31263Propionic anhydrideHCID 30477241-Benzyl-4-(methoxymethyl)-N-phenylpiperidin-4-amine

Product 1

HCID 6454113N-(1-Benzyl-4-(methoxymethyl)-4-piperidyl)-N-phenylpropionamide oxalate

Procedure

A mixture of 7 parts of 4-(methoxymethyl)-N-phenyl-1-(phenylmethyl)-4-piperidinamine and 15 parts of propanoic acid anhydride is stirred and refluxed for 6 hours. After cooling, the reaction mixture is poured onto ice-water and 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 1,1'-oxybisethane and 2-propanol. The sticky salt is triturated in 2-propanone. The product is filtered off and crystallized from 96 parts of acetonitrile, yielding N-[4-(methoxymethyl)-1-(phenylmethyl)-4-piperidinyl]-N-phenylpropanamide ethanedioate; mp. 191.2° 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. customThe sticky salt is triturated in 2-propanone
  10. filtrationThe product is filtered off
  11. customcrystallized from 96 parts of acetonitrile

Sources & evidence

ORD record
ord-e621332264ee4180aecd5f7c63ab7a4f
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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