Propylamine → 3-(4-Methoxy-phenyl)-N-propyl-propionamide

3-(4-methoxyphenyl)-propionic acid (8.8 g, 49 mmol) was refluxed in dichloromethane (200 mL) with thionyl-chloride (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−3300, 2961; 1734, 1642; MS (EI) m/z 221 (M+) Analyses were in agreement with literature data.

1. customThe volatiles were evaporated
2. dissolutionthe resulting oil was dissolved in dichloromethane (100 mL)
3. customwere separated
4. extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
5. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
6. dry with materialwas dried over MgSO4
7. customEvaporation of the solvent

ORD record

ord-f3943d43e1a048808dae1dab81d8c748

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE043244E1