Salicylaldehyde → N,N'-bis-(2-hydroxybenzyl)-2,5-diamino-2,5-dimethyl-hexane

HRID 65832Notes

Reaction equation

HRID 65832 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[NH2:10][C:11]([CH3:19])([CH2:13][CH2:14][C:15]([NH2:18])([CH3:17])[CH3:16])[CH3:12]>C(O)C.[Ni]>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH2:1][NH:10][C:11]([CH3:19])([CH2:13][CH2:14][C:15]([NH:18][CH2:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])([CH3:17])[CH3:16])[CH3:12]

Participants

5

Reactant 2

HCID 6998SalicylaldehydeHCID 901892,5-Hexanediamine, 2,5-dimethyl-

Product 1

HCID 22756075N,N'-bis-(2-hydroxybenzyl)-2,5-diamino-2,5-dimethyl-hexaneYield 34%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

55.0 g of a bisazomethine prepared from 2 mols of salicylaldehyde and 1 mol of 2,5-diamino-2,5-dimethylhexane and with a melting point of 111°-112° C. are hydrogenated for 2 hours in 250 ml of ethanol in an autoclave in the presence of 5.5 g of Raney nickel at 100° C. and under a pressure of 80 atmospheres. The catalyst is filtered off and the filtrate is concentrated. The residue is recrystallised from 220 ml of ispropanol, collected by filtration, washed with n-hexane and dried in vacuo, affording 18.9 g (34% of theory) of N,N'-bis-(2-hydroxybenzyl)-2,5-diamino-2,5-dimethyl-hexane with a melting point of 102°-106° C. Two recrystallisations from a mixture of cyclohexane and ethanol yield 15.2 g of pure product with a melting point of 124°-125° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue is recrystallised from 220 ml of ispropanol
  4. filtrationcollected by filtration
  5. washwashed with n-hexane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-0460bd2a44ee4b5daf634964946d1530
Source dataset
uspto-grants-1978_12
Patent number
US04129556

Reaction notes

Loading…