HCID 19096193, compound → HCID 22414363, compound

Participants

Reaction Steps

A stirred solution of 7.13 g of N-[2-[2-(methylamino)-2-(3-pyridinyl)ethyl]phenyl]-2,2-dimethylpropanamide in 90 ml of 6N hydrochloric acid was refluxed for 5.5 hours and then allowed to stand overnight at room temperature. The solution was decanted over crushed ice, diluted with water (200 ml) and basified with 50% sodium hydroxide solution. The mixture was extracted with dichloromethane (3×150 ml) and the combined, organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to an oil. The oil was purified by preparative HPLC (Water's Associates Prep LC/System 500 A, silica gel, sample applied in dichloromethane, eluted with 2% triethylamine in methanol). Concentration of the appropriate fractions yielded 4.69 g of 2-amino-N-methyl-α-(3-pyridinyl)benzeneethanamine as an oil.

Provenance & Evidence