Sodium Azide → 2,3-Dihydro-7-(phenylmethyl)-2-benzofuranmethanamine

HRID 2116108Notes

Reaction equation

HRID 2116108 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(CC4C=CC=CC=4)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[CH2:33]([C:40]1[C:48]2[O:47][CH:46]([CH2:49][N:50]=[N+]=[N-])[CH2:45][C:44]=2[CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[N-]=[N+]=[N-]>[Pd]>[CH2:33]([C:40]1[C:48]2[O:47][CH:46]([CH2:49][NH2:50])[CH2:45][C:44]=2[CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599065HCID 86599065, compoundHCID 86599181HCID 86599181, compound

Product 1

HCID 689608042,3-Dihydro-7-(phenylmethyl)-2-benzofuranmethanamineYield 79%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-(7-benzyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (6.53 g, 16.6 mmol) with sodium azide (4.30 g, 66.2 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-(7-benzyl-2,3-dihydro-1-benzofuran-2-yl)methyl azide. Treatment of the azide with palladium on carbon (0.40 g, 10 wt. %) generally according to the procedure described for Example 1 gave 3.62 g (79%) of (±)-1-(7-benzyl-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp 107-111° C. (dec); Anal. calcd. for C16H17NOHCl: C, 69.69; H, 6.58; N, 5.08. Found: C, 68.56; H, 6.66; N, 4.92.

Sources & evidence

ORD record
ord-6b25b2e46bbc41d3966c49b695f270ed
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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