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

HRID 2116120Notes

Reaction equation

HRID 2116120 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(C4C=C(Cl)C=C(Cl)C=4)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:34]([CH2:37][CH:38]1[CH2:42][C:41]2[CH:43]=[CH:44][CH:45]=[C:46]([C:47]3[CH:52]=[C:51]([Cl:53])[CH:50]=[C:49]([Cl:54])[CH:48]=3)[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:51]1[CH:52]=[C:47]([C:46]2[C:40]3[O:39][CH:38]([CH2:37][NH2:34])[CH2:42][C:41]=3[CH:43]=[CH:44][CH:45]=2)[CH:48]=[C:49]([Cl:54])[CH:50]=1

Participants

6

Reactant 5

HCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 33558AzideHCID 86599082(+/-)-[7-(3,5-Dichlorophen yl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonateHCID 86599192(+/-)-2-(Azidomethyl)-7-(3,5-dichlorophenyl)-2,3-dihydro-1-benzofuran

Product 1

HCID 11960667(+/-)-1-[7-(3,5-Dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamineYield 49%

Procedure

Treatment of (±)-[7-(3,5-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (0.22 g, 0.498 mmol) with sodium azide (0.08 g, 1.25 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(3,5-dichlorophenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with triphenylphosphine (0.26 g, 0.997 mol) generally according to the procedure described for Example 21 afforded 0.08 g (49%) of (±)-1-[7-(3,5-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 165-168° C.; Anal. calcd. for C15H13Cl2NOHCl: C, 54.49; H, 4.27; N, 4.24. Found: C, 54.27; H, 3.95; N, 4.23.

Sources & evidence

ORD record
ord-eb8e2afc0bc94840b89b4ad2ad8d02cf
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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