Reaction #155360

Reaction equation

N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1,3-propanediamine

allyl p-toluene sulfonate

toluene

→

product

N-allyl-N-methyl-3-[(3-methyl-4-nitrophenyl)amino]-N-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1-propanaminium p-toluene sulfonate

Conditions

Workup

1. 1
   Otherseparated out in the form of an oily substance
2. 2
   OtherThis oil was separated from the supernatant liquid
3. 3
   Otherby decanting
4. 4
   Otherdried
5. 5
   TemperatureOn further cooling the oil
6. 6
   Otherafter drying could
7. 7
   Otherbe crushed

Procedure

N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1,3-propanediamine (60.2 g, 0.14 mol) from step 7.1 was heated under reflux with allyl p-toluene sulfonate (34.0 g, 0.16 mol) in 500 ml toluene for 6 hours. As the reaction progressed the product separated out in the form of an oily substance. This oil was separated from the supernatant liquid by decanting and dried. On further cooling the oil initially solidified to a glassy material and after drying could be crushed to afford the product as a brown powder. Yield: 66.0 g (72.5%).

Source