Sodium Hydroxide → N-(1-cyclopentyl-4-piperidinyl)-3-methyl-N(3-pyridinyl)benzeneacetamide ethanedioate

HRID 236772Notes

Reaction equation

HRID 236772 reaction equation
C(O)(=O)/C=[CH:3]/[C:4]([OH:6])=[O:5].[CH:9]1([N:14]2[CH2:19][CH2:18][CH:17]([N:20]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[C:21](=[O:30])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=3)[CH2:16][CH2:15]2)[CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-:37].[Na+]>>[C:4]([OH:6])(=[O:5])[C:3]([OH:30])=[O:37].[CH:9]1([N:14]2[CH2:19][CH2:18][CH:17]([N:20]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[C:21](=[O:30])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86736173N-(1-cyclopentyl-4-piperidinyl)-3-methyl-N-(3-pyridinyl)benzeneacetamide (E)-2-butenedioate

Product 1

HCID 86736172N-(1-cyclopentyl-4-piperidinyl)-3-methyl-N(3-pyridinyl)benzeneacetamide ethanedioate

Procedure

From 3.9 parts of N-(1-cyclopentyl-4-piperidinyl)-3-methyl-N-(3-pyridinyl)benzeneacetamide (E)-2-butenedioate, the free base is liberated in the conventional manner with a diluted sodium hydroxide solution. After extraction with 2,2'-oxybispropane, the latter is washed with water, dried, filtered and evaporated. The residue is converted into the ethanedioate salt in ethanol. The salt is filtered off and crystallized from a mixture of ethanol and 2,2'-oxybispropane, yielding 3 parts of N-(1-cyclopentyl-4-piperidinyl)-3-methyl-N-(3-pyridinyl)benzeneacetamide ethanedioate; mp. 192.6° C.

Workup

  1. extractionAfter extraction with 2,2'-oxybispropane
  2. washthe latter is washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe salt is filtered off
  7. customcrystallized from a mixture of ethanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-8237c11a36c24c8db65c18c4a4f4ce7c
Source dataset
uspto-grants-1979_06
Patent number
US04157393

Reaction notes

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