Dimethylformamide → N-(2,2-Diethyloxyethyl)-N-phenethyl-3-phenethyloxy-propanamide

3-Phenethyloxypropanoic acid (0.34 g) was dissolved in dichloromethane (20 mL) and treated with oxalyl chloride (0.32 g) and a drop of dimethylformamide at ambient temperature. The resultant solution was stirred at ambient temperature for 2 hours. The solution was then concentrated and azeotroped with dichloromethane (2×20 mL). The collected residue was dissolved in dichloromethane and added, portionwise, to a stirred solution of 2,2-diethoxy-N-phenethyl-ethanamine (0.41 g) and triethylamine (0.6 mL), dissolved in dichloromethane (20 mL), at ambient temperature. The resultant solution was stirred at ambient temperature for 2 hours. The mixture was then concentrated, taken up in ethyl acetate (50 mL), washed with water (2×25 mL), washed with brine (50 mL), dried over anhydrous magnesium sulphate, filtered and concentrated to give the sub-titled compound (0.53 g) as a viscous oil.

1. customat ambient temperature
2. concentrationThe solution was then concentrated
3. customazeotroped with dichloromethane (2×20 mL)
4. dissolutionThe collected residue was dissolved in dichloromethane
5. additionadded
6. dissolutionportionwise, to a stirred solution of 2,2-diethoxy-N-phenethyl-ethanamine (0.41 g) and triethylamine (0.6 mL), dissolved in dichloromethane (20 mL), at ambient temperature
7. concentrationThe mixture was then concentrated
8. washwashed with water (2×25 mL)
9. washwashed with brine (50 mL)
10. dry with materialdried over anhydrous magnesium sulphate
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-67914ed4891946d3b2cbd317d0467dd7

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709511B2