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

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Reaction Steps

Treatment of (±)-(7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (0.40 g, 1.06 mmol) with sodium azide (0.17 g, 2.65 mmol) generally according to the procedure described for Intermediate 98 provided (±)-(7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl azide. Treatment of the azide with palladium on carbon (0.025 g, 10 wt. %) generally according to the procedure described for Example 1 afforded 0.181 g (65%) of (±)-1-(7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp >200° C. (dec); Anal. calcd. for C15H15NOHCl.0.2H2O: C, 67.90; H, 6.23; N, 5.2 Found: C, 67.69; H, 6.16; N, 5.3.

Provenance & Evidence