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

HRID 1659158Notes

Reaction equation

HRID 1659158 reaction equation
[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5]([OH:7])=[O:6])O.[NH2:10][C:11]1[CH:31]=[CH:30][C:14]([C:15]([N:17]([CH:19]2[CH2:23][CH2:22][N:21]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:20]2)[CH3:18])=[O:16])=[CH:13][CH:12]=1.C(O)(=O)/C=C/C(O)=O>C(Cl)(Cl)Cl>[C:1]([OH:9])(=[O:8])/[CH:2]=[CH:4]/[C:5]([OH:7])=[O:6].[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([N:17]([CH:19]2[CH2:23][CH2:22][N:21]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:20]2)[CH3:18])=[O:16])=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 12895722HCID 12895722, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

An aqueous solution containing 3.9 g. (0.0094 mole) of (-) 4-amino-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide malate (Example 68) was extracted with chloroform, the chloroform solution was dried over sodium sulfate and concentrated. The residue was dissolved in ethanol, 1.2 g. (0.01 mole) of fumaric acid added and the solution refrigerated. The fumarate salt which separated weighed 3.3 g. and melted at 205°-207°C. [α]D30 = - 13.89.

Workup

  1. additionAn aqueous solution containing 3.9 g
  2. dry with materialthe chloroform solution was dried over sodium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethanol
  5. customThe fumarate salt which separated

Sources & evidence

ORD record
ord-e3b194c937a64e0bb0c9d2ff57930d81
Source dataset
uspto-grants-1976_06
Patent number
US03966957

Reaction notes

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