Sodium Azide → HCID 11961032, compound

HRID 2116200Notes

Reaction equation

HRID 2116200 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(C4C=CC(OC)=CC=4OC)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:36]([CH2:39][CH:40]1[CH2:44][C:43]2[CH:45]=[CH:46][CH:47]=[C:48]([C:49]3[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][C:50]=3[O:57][CH3:58])[C:42]=2[O:41]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[CH3:58][O:57][C:50]1[CH:51]=[C:52]([O:55][CH3:56])[CH:53]=[CH:54][C:49]=1[C:48]1[C:42]2[O:41][CH:40]([CH2:39][NH2:36])[CH2:44][C:43]=2[CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599142HCID 86599142, compoundHCID 86599246HCID 86599246, compound

Product 1

HCID 11961032HCID 11961032, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-[7-(2,4-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (3.0 g, 6.81 mmol) with sodium azide (1.77 g, 27.26 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(2,4-dimethoxyphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.215 g, 10 wt. %) generally according to the procedure described for Example 1 provided 1.57 g (72%) of (±)-1-[7-(2,4-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 175-178° C.; Anal. calcd. for C17H19NO3HCl: C, 63.45; H, 6.26; N, 4.35. Found: C, 62.59; H, 6.25; N, 4.01.

Sources & evidence

ORD record
ord-c42b8ad0d5694b4da42518d579046794
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…