Reaction #640583

Reaction equation

hydrochloric acid water

3-Aminopropanol

triethylamine

2-nitrobenzyl chloride

→

3-(2-nitrobenzylamino)propanol

Yield 33.2%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureAfter heated
2. 2
   Temperatureto reflux for seven hours
3. 3
   Temperatureto cool
4. 4
   Extractionextracted with ether
5. 5
   Extractionextracted with ethyl acetate
6. 6
   WashThe organic layer was washed with a saturated brine
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   Otherthe solvent was evaporated under reduced pressure

Procedure

3-Aminopropanol (3.94 g, 52.5 mmol) and triethylamine (1.77 g, 17.5 mmol) were dissolved in tetrahydrofuran (30 ml) and added with 2-nitrobenzyl chloride (3.00 g, 17.5 mmol) at room temperature. After heated to reflux for seven hours, the reaction mixture was allowed to cool and poured into 1N hydrochloric acid water and extracted with ether. The aqueous layer was adjusted to pH 9 with a saturated sodium hydrogen carbonate aqueous solution and then extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 3-(2-nitrobenzylamino)propanol (1.22 g).

Source