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

Participants

Reaction Steps

Treatment of (±)-[4-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.31 g, 3.32 mmol) with sodium azide (0.863 g, 13.28 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-4-(2-methylphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.082 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.689 g (85%) of (±)-1-[4-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 231-234° C.; Anal. calcd. for C16H17NOHCl.0.2H2O: C, 68.79; H, 6.64; N, 5.01. Found: C, 68.49; H, 6.50; N, 4.87.

Provenance & Evidence