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

HRID 2116122Notes

Reaction equation

HRID 2116122 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(C4C=CC5C(=CC=CC=5)C=4)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:36]([CH2:39][CH:40]1[CH2:44][C:43]2[CH:45]=[CH:46][CH:47]=[C:48]([C:49]3[CH:58]=[CH:57][C:56]4[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=4)[CH:50]=3)[C:42]=2[O:41]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[CH:50]1[C:51]2[C:56](=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:57]=[CH:58][C:49]=1[C:48]1[C:42]2[O:41][CH:40]([CH2:39][NH2:36])[CH2:44][C:43]=2[CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599081(+/-)-[7-(2-Naphthyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonateHCID 86599194(+/-)-2-(Azidomethyl)-7-(2-naphthyl)-2,3-dihydro-1-benzofuran

Product 1

HCID 68964103(+/-)-1-[7-(2-Naphthyl)-2,3-dihydro-1-benzofuran-2-yl]methanamineYield 48%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-[7-(2-naphthyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (0.51 g, 1.23 mmol) with sodium azide (0.20 g, 3.08 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-7-(2-naphthyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.050 g, 10 wt. %) generally according to the procedure described for Example 1 afforded 0.183 g (48%) of (±)-1-[7-(2-naphthyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 135-140° C.; Anal. calcd. for C19H17NOHCl.0.3H2O: C, 71.94; H, 5.91 N, 4.42. Found: C, 71.67; H, 5.95; N, 4.25.

Sources & evidence

ORD record
ord-f3108fd24c954d06806ddb22ef6c639d
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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