Phenethylamine → HCID 21181135, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 6, Step (a) (0,538 g, 1.91 mmol) was combined with N-benzylmethylamine (0.28 mL, 2.2 mmol), N,N-dimethylformamide (1.3 mL), diisopropylethylamine (0.33 mL, 1.91 mmol), and tetrabutylammonium iodide, and the mixture was then stirred at 70° C. overnight. Upon cooling, the reaction product was diluted with ethyl acetate (50mL) and washed with half-saturated sodium bicarbonate (30 mL). The aqueous layer was extracted with additional ethyl acetate (2×30 mL). The combined organic was dried over MgSO4, and the crude product was concentrated. Silica gel chromatography, using diethyl ether as the eluent, followed by concentration, afforded a product compound as an oil which was characterized by NMR as follows: NMR (free base) (CDCl3, 400 MHz, partial): 3.91 (s, 2H); 2.13 (s, 3H); 1.18 (d, 3H, J=6 Hz); 0.75 (d, 3H, J=6 Hz); Analysis calc'd. for C24H31FN2 : C, 78.64; H, 8.53; N, 7.64; Found: C, 78.54; H, 8.52; N, 7.84

Provenance & Evidence