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

HRID 1658381Notes

Reaction equation

HRID 1658381 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-c04d89058e2c476193f4eb596c14bcac
Source dataset
uspto-grants-1976_06
Patent number
US03963745

Reaction notes

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