Propylenediamine → N,N'-bis-(2-hydroxybenzyl)-propylenediamine

HRID 65831

Reaction equation

HRID 65831 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:10]([NH2:14])[CH:11]([NH2:13])[CH3:12]>C(O)(C)C.[Pt]>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH2:1][NH:14][CH2:10][CH:11]([NH:13][CH2:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])[CH3:12]

Participants

5

Reactant 2

HCID 6567PropylenediamineHCID 6998Salicylaldehyde

Product 1

HCID 15493877N,N'-bis-(2-hydroxybenzyl)-propylenediamineYield 87.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

84.6 g of a bisazomethine prepared from 2 moles of salicylaldehyde and 1 mol of propylenediamine and having a melting point of 57°-58° C. are hydrogenated for 3 hours in 340 ml of isopropanol in an autoclave in the presence of 1.20 g of 5% platinum/charcoal at 45° C. and under a pressure of 50-60 atmospheres. The product crystallises out at room temperature and is dissolved by boiling, with the addition of a further 660 ml of isopropanol. The catalyst is filtered off and the diamine crystallises out on cooling. The crystals are collected by filtration, washed and dried, yielding 75.1 g of N,N'-bis-(2-hydroxybenzyl)-propylenediamine (87.5% of theory); melting point 109°-110° C.

Workup

  1. customThe product crystallises out at room temperature
  2. dissolutionis dissolved
  3. additionby boiling, with the addition of a further 660 ml of isopropanol
  4. filtrationThe catalyst is filtered off
  5. customthe diamine crystallises out
  6. temperatureon cooling
  7. filtrationThe crystals are collected by filtration
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-2c4702a80baf44e485c0b735f74f5f11
Source dataset
uspto-grants-1978_12
Patent number
US04129556

Linked notes

Loading…