Reaction #452466

Reaction equation

N-(4-bromobenzyl)-N-(pyridin-2-yl)pro-pane-1,3-diamine

3-morpholinopropyl isothiocyanate

→

title compound

Yield 76.0%

1-(3-(N-(4-Bromobenzyl)-N-(pyridin-2-yl)amino)propyl)-3-(3-(morpholin-4-yl)propyl)thiourea

Yield 76.0%

Solvents

chloroform

Conditions

Workup

1. 1
   Temperatureat reflux temperature
2. 2
   workup.STIRRINGthe reaction mixture was stirred for an additional 4 h
3. 3
   Temperatureat reflux temperature
4. 4
   OtherThe volatiles were evaporated in vacuo
5. 5
   workup.DISSOLUTIONthe residue (2.05 g) was dissolved in ethyl acetate (20 ml)
6. 6
   workup.WAITleft over night at room temperature
7. 7
   FiltrationThe precipitate was filtered off
8. 8
   Washwashed with ethyl acetate
9. 9
   Otherdried

Procedure

To a solution of N-(4-bromobenzyl)-N-(pyridin-2-yl)pro-pane-1,3-diamine (1.0 g, 3.123 mmol) in chloroform (40 ml) was added 3-morpholinopropyl isothiocyanate (593 mg, 3.123 mmol) and the reaction mixture was stirred for 20 h at reflux temperature. To the reaction mixture was added 10 drops of 3-morpholinopropyl isothiocyanate and the reaction mixture was stirred for an additional 4 h at reflux temperature. The volatiles were evaporated in vacuo and the residue (2.05 g) was dissolved in ethyl acetate (20 ml) and left over night at room temperature. The precipitate was filtered off and washed with ethyl acetate and dried affording 1.20 g (76%) of the title compound as a solid.

Source