Phenethylamine → HCID 58921891, compound

2-(2-Methyl-[1,3]dioxolan-2-yl)-propionic acid of Example 1b (1.60 g, 10 mmol) in dry dichloromethane (15 mL) was cooled to 0° C. under an argon atmosphere. A solution of oxalyl dichloride (2.92 g, 2.0 mL, 23.0 mmol) in dichloromethane (5 mL) was added dropwise. After 5 min at 0° C., the mixture was allowed to warm to room temperature. After stirring for 2 h at room temperature, the excess oxalyl dichloride was removed under reduced pressure to produce a yellow oil which was dissolved in dichloromethane (7 mL). The solution was cooled in an ice bath and phenethylamine (1.12 g, 10.0 mmol) in pyridine (5 mL) was added drop-wise. After the addition was complete, the reaction was warmed to room temperature and allowed to stir overnight. The solution was diluted with dicholoromethane (100 mL) and poured into ice-cold hydrochloric acid (1N, 150 mL). The organic layer was separated and washed with water (100 mL), sodium bicarbonate solution (5%, 50 mL), water (100 mL), and brine (100 mL). After drying with sodium sulfate and concentration on a rotary evaporator, the product was purified by flash chromatography on silica gel, eluting with hexanes-ethyl acetate (3:2) to give 2-(2-methyl-[1,3]dioxolan-2-yl)-N-phenethyl-propionamide (1.81 g, 69%) as colorless crystals.

1. customthe excess oxalyl dichloride was removed under reduced pressure
2. customto produce a yellow oil which
3. temperatureThe solution was cooled in an ice bath
4. additionAfter the addition
5. temperaturethe reaction was warmed to room temperature
6. stirringto stir overnight
7. additionThe solution was diluted with dicholoromethane (100 mL)
8. customThe organic layer was separated
9. washwashed with water (100 mL), sodium bicarbonate solution (5%, 50 mL), water (100 mL), and brine (100 mL)
10. dry with materialAfter drying with sodium sulfate and concentration on a rotary evaporator
11. customthe product was purified by flash chromatography on silica gel
12. washeluting with hexanes-ethyl acetate (3:2)

ORD record

ord-441a3c56471949a893a58cdde12b8671

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07491728B2