Aniline → HCID 21544538, compound

Participants

Reaction Conditions

Reaction Steps

Aniline (1.2 mole, 111.8 grams) was added to a mixture of 2,5-bis(tosyloxymethyl)tetrahydrofuran, represented by formula (II), (0.4 mole, 176.2 grams) and 300 ml of Ansul 161 (triethylene glycol dimethyl ether) and the reaction mixture heated for 4 hours at 185° C. The reaction mixture was cooled to room temperature and neutralized with a methanolic sodium hydroxide solution (32 grams NaOH in 300 ml CH3OH). Sodium tosylate was filtered and Ansul 161 and excess aniline stripped from the filtrate under aspirator pressure. 3-Phenyl-8-oxa-3-azabicyclo(3.2.1)octane, represented by formula (XX), was distilled at 113° C./0.15 mm Hg. The product solidified on standing and after recrystallization from methanol had a melting point of 84°-85° C.

Provenance & Evidence