Triphenylphosphine → (+/-)-1-[7-(2-Chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine

HRID 2116164Notes

Reaction equation

HRID 2116164 reaction equation
CC1C=CC(S(OCC2CC3C=C(F)C=C(C4C=CC=CC=4Cl)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:34]([CH2:37][CH:38]1[CH2:42][C:41]2[CH:43]=[C:44]([F:54])[CH:45]=[C:46]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[Cl:53])[C:40]=2[O:39]1)=[N+]=[N-].[N-]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[Cl:53][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[C:46]1[C:40]2[O:39][CH:38]([CH2:37][NH2:34])[CH2:42][C:41]=2[CH:43]=[C:44]([F:54])[CH:45]=1

Participants

6

Reactant 5

HCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 33558AzideHCID 86599116(+/-)-[5-Fluoro-7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonateHCID 86599224(+/-)-2-(Azidomethyl)-7-(2-chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran

Product 1

HCID 11288935(+/-)-1-[7-(2-Chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamineYield 70%

Procedure

Treatment of (±)-[7-(2-chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (6.65 g, 0.015 mol) with sodium azide (3.99 g, 0.061 mol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(2-chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran. Treatment of the azide with triphenylphosphine (4.18 g, 0.16 mol) generally according to the procedure described for Example 21 provided 3.37 g (70%) of (±)-1-[7-(2-chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp >250° C. (dec); Anal. calcd. for C15H13ClFNOHCl: C, 57.34; H, 4.49; N, 4.46. Found: C, 57.45; H, 4.75; N, 4.22.

Sources & evidence

ORD record
ord-e30f0f96fe8a468f8053a440d3b36fa3
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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