Sodium Azide → (+/-)-1-[4-(2-Methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

HRID 2116097Notes

Reaction equation

HRID 2116097 reaction equation
CC1C=CC(S(OCC2CC3C(C4C=CC=CC=4C)=CC=CC=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:33]([CH2:36][CH:37]1[CH2:41][C:40]2[C:42]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[CH3:52])=[CH:43][CH:44]=[CH:45][C:39]=2[O:38]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[CH3:52][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=1[C:42]1[C:40]2[CH2:41][CH:37]([CH2:36][NH2:33])[O:38][C:39]=2[CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599075(+/-)-[4-(2-Methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonateHCID 86599171(+/-)-2-(Azidomethyl)-4-(2-methylphenyl)-2,3-dihydro-1-benzofuran

Product 1

HCID 68961455(+/-)-1-[4-(2-Methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamineYield 85%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-[4-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.31 g, 3.32 mmol) with sodium azide (0.863 g, 13.28 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-4-(2-methylphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.082 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.689 g (85%) of (±)-1-[4-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 231-234° C.; Anal. calcd. for C16H17NOHCl.0.2H2O: C, 68.79; H, 6.64; N, 5.01. Found: C, 68.49; H, 6.50; N, 4.87.

Sources & evidence

ORD record
ord-31093ba36f184c048c935ddc4f3a165f
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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