Sodium Azide → (+/-)-1-[7-(4-Chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

HRID 2116147Notes

Reaction equation

HRID 2116147 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[C:15]=3[O:14]2)(=O)=O)=CC=1.[N-:29]=[N+]=[N-].[Na+].N(CC1CC2C=CC=C(C3C=CC(F)=CC=3)C=2O1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pt]>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]2[C:15]3[O:14][CH:13]([CH2:12][NH2:29])[CH2:17][C:16]=3[CH:18]=[CH:19][CH:20]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599102(+/-)-[7-(4-Chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonateHCID 86599212(+/-)-2-(Azidomethyl)-7-(4-fluorophenyl)-2,3-dihydro-1-benzofuran

Product 1

HCID 11572460(+/-)-1-[7-(4-Chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamineYield 78.9%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

Treatment of (±)-[7-(4-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.2 g, 2.89 mmol) with sodium azide (0.752 g, 11.57 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(4-fluorophenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with sulfided platinum on carbon (0.082 g, 5 wt. %) generally according to the procedure described for Example 1 provided 0.592 g (69%) of (±)-1-[7-(4-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 212-214° C.; Anal. calcd. for C15H14ClNOHCl: C, 60.83; H, 65.10; N, 4.73. Found: C, 59.99; H, 5.00; N, 4.47.

Sources & evidence

ORD record
ord-0ea84e5599c648dd8061995174f2b7be
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…