Ammonium Hydroxide → HCID 12298215, compound

HRID 1448277Notes

Reaction equation

HRID 1448277 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)[CH3:2].[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:3])=[O:34].[CH2:1]([O:3][CH2:4][C:5]1([N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25](=[O:28])[CH2:26][CH3:27])[CH2:6][CH2:7][N:8]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:9][CH2:10]1)[CH3:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 31263Propionic anhydrideHCID 12298206HCID 12298206, compound

Product 1

HCID 12298215HCID 12298215, compound

Procedure

A mixture of 17.5 parts of 4-(ethoxymethyl)-N-phenyl-1-(phenylmethyl)-4-piperidinamine and 36 parts of propionic acid anhydride is stirred and refluxed for 6 hours. The reaction mixture is poured onto ice-water and the whole is basified with ammonium hydroxide. The product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is converted into the ethanedioate salt in 2-propanone. The salt is filtered off and crystallized from 2-propanol (135 parts). The product is filtered off and dried, yielding N-[4-(ethoxymethyl)-1-(phenylmethyl)-4-piperidinyl]-N-phenylpropanamide ethanedioate; mp. 181.2° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. additionThe reaction mixture is poured onto ice-water
  3. extractionThe product is extracted with trichloromethane
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe salt is filtered off
  9. customcrystallized from 2-propanol (135 parts)
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-74a11b34e4e747dc9f4854af49098061
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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