Sodium Hydroxide → N-[4-(hydroxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide propanoate ethanedioate

HRID 1973831Notes

Reaction equation

HRID 1973831 reaction equation
[C:1]1([NH:7][C:8]2([CH2:22][OH: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:24]([O:28][C:29](=[O:32])[CH2:30][CH3:31])(=[O:27])[CH2:25][CH3:26].[OH-:33].[Na+]>>[C:29]([OH:28])(=[O:32])[C:30]([OH:23])=[O:33].[C:24]([OH:28])(=[O:27])[CH2:25][CH3:26].[OH:23][CH2:22][C:8]1([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:29](=[O:32])[CH2:30][CH3:31])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 31263Propionic anhydrideHCID 122982044-Piperidinemethanol, 4-(phenylamino)-1-(2-phenylethyl)-

Product 1

HCID 86734312N-[4-(hydroxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide propanoate ethanedioate

Procedure

A mixture of 8 parts of 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinemethanol and 35 parts of propanoic acid anhydride is stirred and refluxed for 3 hours. After cooling, the reaction mixture is poured onto 300 parts of ice-water and the whole is alkalized with sodium hydroxide solution. The product is extracted with 1,1'-oxybisethane. The extract is washed with water, dried, filtered and evaporated. The residue is dissolved in 140 parts of 2,2'-oxybispropane 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-propanone. The salt is filtered off and dried, yielding N-[4-(hydroxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide propanoate ethanedioate; mp. 182° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionThe product is extracted with 1,1'-oxybisethane
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe residue is dissolved in 140 parts of 2,2'-oxybispropane
  9. stirringthe solution is stirred with activated charcoal
  10. filtrationThe latter is filtered off
  11. customthe filtrate is evaporated
  12. filtrationThe salt is filtered off
  13. customdried

Sources & evidence

ORD record
ord-50ec72f08da645e1adb44ff4672695eb
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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