Ammonium Hydroxide → N-[4-acetyl-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide ethanedioate

HRID 1448328Notes

Reaction equation

HRID 1448328 reaction equation
[C:1]1([NH:7][C:8]2([C:22](=[O:24])[CH3:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25]([O:29][C:30](=[O:33])[CH2:31]C)(=[O:28])[CH2:26][CH3:27].[OH-:34].[NH4+]>>[C:30]([OH:29])(=[O:33])[C:31]([OH:24])=[O:34].[C:22]([C:8]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:25](=[O:28])[CH2:26][CH3:27])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)(=[O:24])[CH3:23]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 31263Propionic anhydrideHCID 191586Demethylfentanyl

Product 1

HCID 12298121N-[4-acetyl-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide ethanedioate

Conditions

Temperature
180 °C

Procedure

A mixture of 4.8 parts of 1-[4-(phenylamino)-1-(2-phenylethyl)-4-piperidinyl]ethanone and 15 parts of propanoic acid, anhydride is stirred for 5 hours at 180° C. (oil-bath). Stirring is continued overnight, while meantime the mixture is allowed to reach room temperature. The reaction mixture is poured onto ice-water and the whole is alkalized with a concentrated ammonium hydroxide solution. The product is extracted with benzene. The extract is washed twice with water, dried, filtered and evaporated in vacuo. The residue is dissolved in 1,1'-oxybisethane and the solution is stirred with activated charcoal. The latter is filtered off and the filtrate is evaporated. The residue is converted into the ethanedioate salt in 2-propanol. The salt is filtered off and crystallized from 2-propanol, yielding N-[4-acetyl-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide ethanedioate; mp. 196.8° C.

Workup

  1. stirringStirring
  2. waitis continued overnight, while meantime
  3. customto reach room temperature
  4. additionThe reaction mixture is poured onto ice-water
  5. extractionThe product is extracted with benzene
  6. washThe extract is washed twice with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. dissolutionThe residue is dissolved in 1,1'-oxybisethane
  11. stirringthe solution is stirred with activated charcoal
  12. filtrationThe latter is filtered off
  13. customthe filtrate is evaporated
  14. filtrationThe salt is filtered off
  15. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-72c0b95194e544dcb26bbf0229fb1c39
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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