Salicylaldehyde → N,N'-Bis-(2-hydroxybenzyl)-hexamethylenediamine

HRID 65829

Reaction equation

HRID 65829 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17]>C(O)(C)C.[Ni]>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH2:1][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

Participants

5

Reactant 2

HCID 6998SalicylaldehydeHCID 16402Hexamethylenediamine

Product 1

HCID 1957305N,N'-Bis-(2-hydroxybenzyl)-hexamethylenediamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

122.1 g of a bisazomethine prepared from 2 mols of salicylaldehyde and 1 mol of hexamethylenediamine and having a melting point of 72°-73° C. are hydrogenated in 550 ml of isopropanol in an autoclave in the presence of 8 g of Raney nickel at 75° C. and under a pressure of 90 atmospheres. The product crystallises out at room temperature and is dissolved by boiling with the addition of a further 650 ml of isopropanol. The catalyst is filtered off, and N,N'-bis-(2-hydroxybenzyl)hexamethylenediamine crystallises out on cooling.

Workup

  1. customThe product crystallises out at room temperature
  2. dissolutionis dissolved
  3. additionby boiling with the addition of a further 650 ml of isopropanol
  4. filtrationThe catalyst is filtered off
  5. customN,N'-bis-(2-hydroxybenzyl)hexamethylenediamine crystallises out
  6. temperatureon cooling

Sources & evidence

ORD record
ord-91367ad1c6eb45eeb010593806d03789
Source dataset
uspto-grants-1978_12
Patent number
US04129556

Linked notes

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