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

Participants

Reaction Steps

Treatment of (±)-[7-(2-naphthyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (0.51 g, 1.23 mmol) with sodium azide (0.20 g, 3.08 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-7-(2-naphthyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.050 g, 10 wt. %) generally according to the procedure described for Example 1 afforded 0.183 g (48%) of (±)-1-[7-(2-naphthyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 135-140° C.; Anal. calcd. for C19H17NOHCl.0.3H2O: C, 71.94; H, 5.91 N, 4.42. Found: C, 71.67; H, 5.95; N, 4.25.

Provenance & Evidence