Butyric anhydride → N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylbutanamide ethanedioate

HRID 1448325Notes

Reaction equation

HRID 1448325 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1.[C:25]([O:30][C:31](=[O:35])[CH2:32]CC)(=[O:29])[CH2:26][CH2:27][CH3:28].[OH-:36].[NH4+]>>[C:31]([OH:30])(=[O:35])[C:32]([OH:2])=[O:36].[CH3:1][O:2][CH2:3][C:4]1([N:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:25](=[O:29])[CH2:26][CH2:27][CH3:28])[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 7798Butyric anhydrideHCID 14923Ammonium HydroxideHCID 122982104-Piperidinamine, 4-(methoxymethyl)-N-phenyl-1-(2-phenylethyl)-

Product 1

HCID 12298012N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylbutanamide ethanedioate

Procedure

A mixture of 3 parts of 4-(methoxymethyl)-N-phenyl-1-(2-phenylethyl)-4-piperidinamine and 5 parts of butanoic acid, anhydride is stirred and refluxed for 8 hours. The reaction mixture is poured onto 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 stirred in 1,1'-oxybisethane with activated charcoal. The latter is filtered off and the filtrate is evaporated. The residue is converted into the ethanedioate salt 2-propanol. The salt is filtered off and crystallized from 2-propanone, yielding 1.7 parts of N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylbutanamide ethanedioate; mp. 174.2° C.

Workup

  1. temperaturerefluxed for 8 hours
  2. additionThe reaction mixture is poured onto water
  3. extractionThe product is extracted with trichloromethane
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. stirringThe oily residue is stirred in 1,1'-oxybisethane with activated charcoal
  9. filtrationThe latter is filtered off
  10. customthe filtrate is evaporated
  11. filtrationThe salt is filtered off
  12. customcrystallized from 2-propanone

Sources & evidence

ORD record
ord-07a33bbfcf4b429bb2f7bfc7b46febca
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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