HCID 86599209, compound → HCID 11960862, compound

HRID 2116141Notes

Reaction equation

HRID 2116141 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[C:7]=2[O:6]1)=[N+]=[N-]>[Pd]>[CH3:21][O:20][C:16]1[CH:15]=[C:14]([C:13]2[C:7]3[O:6][CH:5]([CH2:4][NH2:1])[CH2:9][C:8]=3[CH:10]=[CH:11][CH:12]=2)[CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 86599209HCID 86599209, compound

Product 1

HCID 11960862HCID 11960862, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-[7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (3.0 g, 7.82 mmol) with sodium azide (0.309 g, 4.48 mmol) generally according to the procedure described for Intermediate 98 gave (±)-2-(azidomethyl)-7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.030 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.25 g (80%) of (±)-1-[7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 152-154° C.; Anal. calcd. for C16H17NO2HCl: C, 65.86; H, 6.22; N, 4.8. Found: C, 65.21; H, 6.17; N, 4.46.

Sources & evidence

ORD record
ord-b0e7c1bfac124d76a103ddd04b172fa0
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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