Sodium Hydroxide → 4-Amino-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide (2E)-2-butenedioate (1:1)

HRID 1659159Notes

Reaction equation

HRID 1659159 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH2:9][C:10]1[CH:30]=[CH:29][C:13]([C:14]([N:16]([CH:18]2[CH2:22][CH2:21][N:20]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:19]2)[CH3:17])=[O:15])=[CH:12][CH:11]=1.[OH-].[Na+].C(O)(=O)/C=C/C(O)=O>C(O)C.CO>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[NH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([N:16]([CH:18]2[CH2:22][CH2:21][N:20]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:19]2)[CH3:17])=[O:15])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 68132583HCID 68132583, compound

Product 1

HCID 53841464-Amino-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide (2E)-2-butenedioate (1:1)

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

An aqueous solution of 2.2 g. (0.005 mole) of (+) 4-amino-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide maleate was made basic using sodium hydroxide and the basic solution was extracted with chloroform. The dried chloroform solution was concentrated and the residue treated with a solution of 0.6 g. (0.005 mole) of fumaric acid in ethanol-methanol. The fumarate salt which separated weighed 1.6 g. and melted at 204°-206°C. [α]D30 = + 12.72.

Workup

  1. extractionthe basic solution was extracted with chloroform
  2. concentrationThe dried chloroform solution was concentrated
  3. additionthe residue treated with a solution of 0.6 g
  4. customThe fumarate salt which separated

Sources & evidence

ORD record
ord-05b6fa99b4d544b1ab17400b22521290
Source dataset
uspto-grants-1976_06
Patent number
US03966957

Reaction notes

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