Reaction #1747829

Reaction equation

NaOH

n-propylamine

3-(4-methoxyphenyl)-propionic acid

thionylchloride

→

amide

3-(4-methoxyphenyl)-propionic acid n-propylamide

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   OtherThe volatiles were evaporated
2. 2
   workup.DISSOLUTIONthe resulting oil was dissolved in dichloromethane (100 mL)
3. 3
   Otherwere separated
4. 4
   Extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
5. 5
   WashThe combined organic layers were washed with water (50 mL) and brine (50 mL)
6. 6
   Dryingwas dried over MgSO4
7. 7
   OtherEvaporation of the solvent

Procedure

3-(4-methoxyphenyl)-propionic acid (8.8 g, 49 mmol) was refluxed in dichloromethane (200 mL) with thionylchloride (6.6 mL, 90 mmol) for 1 h. The volatiles were evaporated and the resulting oil was dissolved in dichloromethane (100 mL). This was added to a vigorously stirred mixture of 5% aqueous NaOH (200 mL), dichloromethane (100 mL) and n-propylamine (3.0 mL, 71 mmol). After stirring for 1 h the layers were separated and the aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL) and was dried over MgSO4. Evaporation of the solvent gave the amide in quantitative yield (10.7 g, 49 mmol, 100%). IR (neat) cm−1 3300, 2961; 1734, 1642; MS (EI) m/z 221 (M+) Analyses were in agreement with literature data.

Source