Sodium Hydroxide → (4-Aminomethylbenzyl)-(4-dipropylaminomethylphenyl)-amine

HRID 1173886Notes

Reaction equation

HRID 1173886 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]2[CH:34]=[CH:33][C:20]([CH2:21][N:22]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].O.NN.[OH-].[Na+]>CO>[NH2:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][NH:15][C:12]2[CH:13]=[CH:14][C:9]([CH2:8][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])=[CH:10][CH:11]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 210843762-{4-[(4-Dipropylaminomethylphenylamino)methyl]benzyl}isoindole-1,3-dione

Product 1

HCID 23079293(4-Aminomethylbenzyl)-(4-dipropylaminomethylphenyl)-amineYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The compound (521.6 mg) obtained in Example 39-1 was dissolved in methanol (15 ml) and added with hydrazine monohydrate (0.11 ml), followed by stirring at 60° C. for 1.5 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then subjected to extraction with chloroform. Subsequently, the organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. After the solvent had been distilled off, the subject compound (372 mg) was obtained as a yellow solid.

Workup

  1. extractionsubjected to extraction with chloroform
  2. washSubsequently, the organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationAfter the solvent had been distilled off

Sources & evidence

ORD record
ord-936a9b2789f2401a82e4e1577315b761
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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