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 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.

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-069eb298129942f4944fecc3ed51af3a

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06683087B2