Dichloromethane → HCID 10149879, compound

Participants

Reaction Steps

To a solution containing the compound of example 29 (0.345 g, 0.80 mmol) dissolved in methylene chloride (1.2 mL) were added trifluoromethane sulfonic acid (0.496 mL, 5.6 mmol) and anisole (0.261 mL, 2.4 mmol) at room temperature. After 1 hour, the reaction was completed and the reaction mixture was basified to a pH of 12 with 1N NaOH. Water and methylene chloride were added and the reaction mixture was stirred for 45 minutes. The contents of the flask were transferred to a separatory funnel, and the aqueous layer was extracted with methylene chloride (4×). The combined organic layers were dried with magnesium sulfate, filtered and concentrated to give yellow oil. Further purification (10% ammonia in 2M solution of ethanol/Ethyl acetate) yielded 0.190 g of the free amine product (80%). The free amine was then taken and converted into the hydrochloride salt. After the compound was dissolved in diethyl ether, HCl in a 2M solution in diethyl ether (0.32 mL, 0.64 mmol) was added. After the mixture stirred for 30 minutes, the resulting yellow precipitate was filtered off to give 0.1932 g of the desired product.

Provenance & Evidence