Dichloromethane → HCID 21904822, compound

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Reaction Steps

The compound from Example 5 (0.200 g, 0.53 mmol) was dissolved in methylene chloride (0.5 mL). Trifluoromethane sulfonic acid (0.0.329 mL, 3.72 mmol) and anisole (0.115 mL, 1.06 mmol) were added at 0° C. After 2 hours, another portion of trifluoromethane sulfonic acid (2 eq.) was added. After a total of 4 hours, the reaction was completed. 1 N NaOH was added to quench the reaction (pH=9–10). The contents of the flask were transferred to a separatory funnel with methylene chloride and water, and extracted with methylene chloride (3×). The combined organic extracts were dried with magnesium sulfate, filtered and concentrated to give a brown oil, crude desired product. Further purification (10% ammonia in 2M solution of methanol/ethyl acetate) yielded 0.067 g of desired product (52%). The free amine product (0.0605 g, 0.249 mmol) was then dissolved in diethyl ether, and a 2M solution of hydrogen chloride (0.137 mL, 0.274 mmol) was added. After 40 minutes, the yellow precipitate was filtered off to give the desired product.

Provenance & Evidence