Sodium Azide → HCID 11960767, compound

HRID 2116131Notes

Reaction equation

HRID 2116131 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(C4C(C)=CC=CC=4C)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[C:52]([CH3:53])=[CH:51][CH:50]=[CH:49][C:48]=3[CH3:54])[C:40]=2[O:39]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[CH3:54][C:48]1[CH:49]=[CH:50][CH:51]=[C:52]([CH3:53])[C:47]=1[C:46]1[C:40]2[O:39][CH:38]([CH2:37][NH2:34])[CH2:42][C:41]=2[CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599089HCID 86599089, compoundHCID 86599202HCID 86599202, compound

Product 1

HCID 11960767HCID 11960767, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-[7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (0.646 g, 1.58 mmol) with sodium azide (0.411 g, 6.33 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.057 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.383 g (84%) of (±)-1-[7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp >250° C.; Anal. calcd. for C17H19NOHCl: C, 70.46; H, 6.96; N, 4.83. Found: C, 69.06; H, 7.01; N, 4.21.

Sources & evidence

ORD record
ord-be1e67df4192449685d2f1139fc6fb91
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…