HCID 86599109, compound → HCID 11960945, compound

HRID 2116160Notes

Reaction equation

HRID 2116160 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:9][C:8]2[CH:10]=[C:11]([Cl:19])[CH:12]=[C:13]([C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)[C:7]=2[O:6]1)=[N+]=[N-]>[Pt]>[Cl:19][C:11]1[CH:12]=[C:13]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[C:7]2[O:6][CH:5]([CH2:4][NH2:1])[CH2:9][C:8]=2[CH:10]=1

Participants

3

Reactant 1

HCID 86599109HCID 86599109, compound

Product 1

HCID 11960945HCID 11960945, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

Treatment of (±)-(5-chloro-7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (0.18 g, 0.43 mmol) with sodium azide (0.11 g, 1.72 mmol) generally according to the procedure described for Intermediate 98 provided 0.13 g of (±)-2-(azidomethyl)-5-chloro-7-thien-3-yl-2,3-dihydro-1-benzofuran. Treatment of the azide with sulfided platinum on carbon (120 mg, 5 wt. %) generally according to the procedure described for Example 1 gave 0.11 g (85%) of (±)-(5-chloro-7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methylamine as a light yellow solid, hydrochloride salt. mp 230° C. (dec); Anal. calcd. for C13H12ClNOSHCl: C, 51.66; H, 4.34; N, 4.63. Found: C, 45.27; H, 4.19; N, 3.93.

Sources & evidence

ORD record
ord-2d3c6d7cdafc4e1687689884e257f787
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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