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

HRID 2116121Notes

Reaction equation

HRID 2116121 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(C4C=CC=CC=4)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[C:32]1([C:38]2[C:46]3[O:45][CH:44]([CH2:47][N:48]=[N+]=[N-])[CH2:43][C:42]=3[CH:41]=[CH:40][CH:39]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[N-]=[N+]=[N-]>[Pd]>[C:32]1([C:38]2[C:46]3[O:45][CH:44]([CH2:47][NH2:48])[CH2:43][C:42]=3[CH:41]=[CH:40][CH:39]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599080(+/-)-(7-Phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 86599193(+/-)-(7-Phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl azide

Product 1

HCID 11960668(+/-)-1-(7-Phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamineYield 65%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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.

Sources & evidence

ORD record
ord-478b28986a124a98bc377cf05af4880d
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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