Hydrochloric Acid → HCID 131719124, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 2, Step (b) (2.61 g, 10.3 mmol) was diluted with dimethylformamide (6 mL). N-benzylmethylamine (1.42 mL, 11 mmol), diisopropylethylamine (1.91 mL, 11 mmol) and tetrabutylammoniumbromide (300 mg) were added and the mixture was stirred at 57° C. overnight, then at 77° C. for an additional 24 hours. The mixture was diluted with water (10 ml) and extracted with ethylacetate (100 mL, then 2×10 mL). The combined organic layers were dried over MgSO4, filtered through silica, and concentrated. Chromatography in silica gel afforded the free base, which was converted to the hydrochloride salt using hydrogen chloride gas in dichloromethane. The salt was recrystallized from a mixture of dichloromethane, methyl acetate and hexane, and characterized by NMR as follows: Analysis calcd. for C22H28ClFN2 : C, 70.48; H, 7.53; N, 7.47; Found: C, 70.09; H, 7.52; N, 7.33; 13CNMR free base (CDCl3, 100 MHz, partial): 62.2, 56.5, 53.1, 42.1, 37.9, 35.5, 23.4, 18.8, 18.6.

Provenance & Evidence