Sodium Azide → (+/-)-1-[7-(4-Chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

Participants

Reaction Steps

Treatment of (±)-[7-(4-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.2 g, 2.89 mmol) with sodium azide (0.752 g, 11.57 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(4-fluorophenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with sulfided platinum on carbon (0.082 g, 5 wt. %) generally according to the procedure described for Example 1 provided 0.592 g (69%) of (±)-1-[7-(4-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 212-214° C.; Anal. calcd. for C15H14ClNOHCl: C, 60.83; H, 65.10; N, 4.73. Found: C, 59.99; H, 5.00; N, 4.47.

Provenance & Evidence