Sodium Azide → HCID 68966371, compound

HRID 2116109Notes

Reaction equation

HRID 2116109 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(C(C)C)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[CH:29]([C:32]1[C:40]2[O:39][CH:38]([CH2:41][N:42]=[N+]=[N-])[CH2:37][C:36]=2[CH:35]=[CH:34][CH:33]=1)([CH3:31])[CH3:30].[N-]=[N+]=[N-]>[Pd]>[CH:29]([C:32]1[C:40]2[O:39][CH:38]([CH2:41][NH2:42])[CH2:37][C:36]=2[CH:35]=[CH:34][CH:33]=1)([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 19749590HCID 19749590, compoundHCID 86599182HCID 86599182, compound

Product 1

HCID 68966371HCID 68966371, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-(7-isopropyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (5.15 g, 14.9 mmol) with sodium azide (3.87 g, 59.5 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-(7-isopropyl-2,3-dihydro-1-benzofuran-2-yl)methyl azide. Treatment of the azide with palladium on carbon (0.30 g, 10 wt. %) generally according to the procedure described for Example 1 gave 2.35 g (69%) of (±)-(7-isopropyl-2,3-dihydro-1-benzofuran-2-yl)methylamine as a white solid, hydrochloride salt. mp 160-164° C. (dec); Anal. calcd. for C12H17NOHCl: C, 63.29; H, 7.97; N, 6.15. Found: C, 63.33; H, 7.98; N, 6.15.

Sources & evidence

ORD record
ord-0264889e70874d49b54fdf12578eaa41
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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