HCID 86599187, compound → HCID 68964091, compound

HRID 2116115Notes

Reaction equation

HRID 2116115 reaction equation
[C:1]1([C:7]2[CH:19]=[CH:18][C:10]3[CH2:11][CH:12]([CH2:14][N:15]=[N+]=[N-])[O:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd]>[C:1]1([C:7]2[CH:19]=[CH:18][C:10]3[CH2:11][CH:12]([CH2:14][NH2:15])[O:13][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 86599187HCID 86599187, compound

Product 1

HCID 68964091HCID 68964091, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-(6-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (0.280 g, 0.736 mmol) with sodium azide (0.191 g, 2.94 mmol) generally according to the procedure described for Intermediate 98 gave (±)-(6-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl azide. Treatment of the azide with palladium on carbon (0.026 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.190 g (90%) of (±)-(6-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine as a tan solid, hydrobromide salt. mp 218-221° C. Anal. calcd. for C15H15NOHBr: C, 58.84; H, 5.27; N, 4.57. Found: C, 54.80; H, 4.88; N, 4.18.

Sources & evidence

ORD record
ord-7381a10f82a44d97b44af7da878e20cb
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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