Dimethylformamide → N-Benzyl-N-(2,2-diethoxyethyl)-3-phenethyloxy-propanamide

3-Phenethyloxypropanoic acid (0.4 g) was dissolved in dichloromethane (10 mL) and treated with oxalyl chloride (0.35 g) and a drop of dimethylformamide at ambient temperature. The resultant solution was stirred at ambient temperature for 1 hour. The solution was then concentrated and azeotroped with dichloromethane (3×10 mL). The collected residue was dissolved in dichloromethane (5 mL) and added, portionwise, to a stirred solution of N-benzyl-2,2-diethoxy-ethanamine (0.47 g) and N-ethyl-N-isopropyl-propan-2-amine (0.6 mL), dissolved in dichloromethane (10 mL), at ambient temperature. The resultant solution was stirred at ambient temperature for 1 hour. The mixture was then poured into ethyl acetate (25 mL), washed with water (2×25 mL), washed with brine (25 mL), dried over anhydrous magnesium sulphate, filtered and concentrated to give the sub-titled compound (0.62 g) as an oil.

1. customat ambient temperature
2. concentrationThe solution was then concentrated
3. customazeotroped with dichloromethane (3×10 mL)
4. dissolutionThe collected residue was dissolved in dichloromethane (5 mL)
5. additionadded
6. dissolutionportionwise, to a stirred solution of N-benzyl-2,2-diethoxy-ethanamine (0.47 g) and N-ethyl-N-isopropyl-propan-2-amine (0.6 mL), dissolved in dichloromethane (10 mL), at ambient temperature
7. additionThe mixture was then poured into ethyl acetate (25 mL)
8. washwashed with water (2×25 mL)
9. washwashed with brine (25 mL)
10. dry with materialdried over anhydrous magnesium sulphate
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-c67f40178cb64c82a1dd5ad97f9ed90e

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709511B2