Sodium Hydroxide → HCID 9903877, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-benzyl-N-[2-(3-chloro-1H-indol-4-yloxy)-ethyl]-carbamic acid tert-butyl ester (5.4 g, 13.5 mmol) in methoxyethanol (25 mL) containing 85% phosphoic acid (10 mL) was heated to 100° C. for 1 hour. The reaction was allowed to cool and then basified with 2N sodium hydroxide and extracted with methylene chloride (2×150 mL). The organic layer dried over anhydrous magnesium sulfate, filtered and chromatographed (5% methanol-methylene chloride) to afford 3.28 g of a grayish-white solid (86.1%): mp 145°-146° C. The fumarate salt was prepared in isopropanol: mp 220°-221° C.

Provenance & Evidence