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

HRID 2116129Notes

Reaction equation

HRID 2116129 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(C4C=CC=CC=4F)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:33]([CH2:36][CH:37]1[CH2:41][C:40]2[CH:42]=[CH:43][CH:44]=[C:45]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[F:52])[C:39]=2[O:38]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pt]>[F:52][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=1[C:45]1[C:39]2[O:38][CH:37]([CH2:36][NH2:33])[CH2:41][C:40]=2[CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599085(+/-)-[7-(2-Fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonateHCID 86599200(+/-)-2-(Azidomethyl)-7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran

Product 1

HCID 11960765(+/-)-1-[7-(2-Fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamineYield 83%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

Treatment of (±)-[7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (3.13 g, 7.85 mmol) with sodium azide (2.04 g, 31.42 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with sulfided platinum on carbon (0.21 g, 5 wt. %) generally according to the procedure described for Example 1 provided 1.81 g (83%) of (±)-1-[7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 244-246° C.; Anal. calcd. for C15H14FNOHCl: C, 64.4; H, 5.4; N, 5.01. Found: C, 63.98; H, 5.4; N, 4.89.

Sources & evidence

ORD record
ord-d8ad60d9e6bc4e709fcd2676f85f39e2
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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