HCID 86599214, compound → HCID 11960868, compound

HRID 2116152Notes

Reaction equation

HRID 2116152 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][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[C:7]=2[O:6]1)=[N+]=[N-]>[Pt]>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C:13]1[C:7]2[O:6][CH:5]([CH2:4][NH2:1])[CH2:9][C:8]=2[CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 1

HCID 86599214HCID 86599214, compound

Product 1

HCID 11960868HCID 11960868, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

Treatment of (±)-[7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (4.2 g, 9.34 mmol) with sodium azide (2.4 g, 37.38 mmol) generally according to the procedure described for Intermediate 98 gave (±)-2-(azidomethyl)-7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with sulfided platinum on carbon (0.32 g, 5 wt. %) generally according to the procedure described for Example 1 provided 2.16 g (72%) of (±)-1-[7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 198-200° C.; Anal. calcd. for C15H13Cl2NOHCl: C, 54.49; H, 4.27; N, 4.24. Found: C, 54.5; H, 4.39; N, 4.16.

Sources & evidence

ORD record
ord-5c2b271bb9bd4a838c257371627d7e12
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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