Phthalimide → Bis(p-aminocyclohexyl)methane phthalamide

HRID 2166920

Reaction equation

HRID 2166920 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]2)[CH2:4][CH2:3]1.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12>O>[C:16]([NH2:20])(=[O:26])[C:17]1[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:19]([NH2:1])=[O:21].[NH2:1][CH:2]1[CH2:3][CH2:4][CH:5]([CH2:8][CH:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6809Phthalimide2×HCID 156604,4'-Diaminodicyclohexylmethane

Product 1

HCID 20497350Bis(p-aminocyclohexyl)methane phthalamideYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bis(p-aminocyclohexyl)methane phthalamide was prepared by the aqueous reaction of bis(p-aminocyclohexyl)methane with phthalimide, according to a procedure similar to that published by Spring and Woods noted hereinabove. Thus, an emulsion of the amine in water was made using vigorous stirring. Phthalimide (1.0 mole per 2.4 moles of amine) was finely grounded and added to the emulsion at room temperature within a 10-minute period. The mixture was stirred for an additional 40 minutes and poured into a separatory funnel and extracted with chloroform. The chloroform solution was dried over magnesium sulfate, filtered and stripped. The product was washed with hexane and with anhydrous ethyl ether and then stripped in a vacuum oven.

Workup

  1. additionadded to the emulsion at room temperature within a 10-minute period
  2. additionpoured into a separatory funnel
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform solution was dried over magnesium sulfate
  5. filtrationfiltered
  6. washThe product was washed with hexane and with anhydrous ethyl ether

Sources & evidence

ORD record
ord-5822d7cb160f442cbccdc950b03a82a4
Source dataset
uspto-grants-1983_06
Patent number
US04390679

Linked notes

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