Sodium Hydroxide → N-[1-(1-methylethyl)-4-piperidinyl]N-phenyl-2-thiopheneacetamide ethanedioate

HRID 26765Notes

Reaction equation

HRID 26765 reaction equation
C(O)(=O)/C=[CH:3]/[C:4]([OH:6])=[O:5].[CH3:9][CH:10]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:19](=[O:26])[CH2:20][C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)[CH2:14][CH2:13]1)[CH3:11].[OH-:33].[Na+]>>[C:4]([OH:6])(=[O:5])[C:3]([OH:26])=[O:33].[CH3:11][CH:10]([N:12]1[CH2:13][CH2:14][CH:15]([N:18]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:19](=[O:26])[CH2:20][C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)[CH2:16][CH2:17]1)[CH3:9]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86736487N-[1-(1-methylethyl)-4-piperidinyl]-N-phenyl-2-thiopheneacetamide (E)-2-butenedioate

Product 1

HCID 86736486N-[1-(1-methylethyl)-4-piperidinyl]N-phenyl-2-thiopheneacetamide ethanedioate

Procedure

From 6 parts of N-[1-(1-methylethyl)-4-piperidinyl]-N-phenyl-2-thiopheneacetamide (E)-2-butenedioate, the free base is liberated in the conventional manner with a diluted sodium hydroxide solution. 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-propanol. The salt is filtered off and dried, yielding 3.2 parts of N-[1-(1-methylethyl)-4-piperidinyl]N-phenyl-2-thiopheneacetamide ethanedioate; mp. 167.4° C.

Workup

  1. extractionThe product is extracted with trichloromethane
  2. washThe extract is washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe salt is filtered off
  7. customdried

Sources & evidence

ORD record
ord-e2ebac27ce36440aa591fae102c93ae1
Source dataset
uspto-grants-1979_04
Patent number
US04151286

Reaction notes

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