Hydrochloric Acid → (+)-1-(4-Phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine

HRID 2116096Notes

Reaction equation

HRID 2116096 reaction equation
CC1C=CC(S(OCC2CC3C(C4C=CC=CC=4)=CC=CC=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[C:32]1([C:38]2[C:43]3[CH2:44][CH:45]([CH2:47][N:48]=[N+]=[N-])[O:46][C:42]=3[CH:41]=[CH:40][CH:39]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[N-]=[N+]=[N-].Cl>C(O)C.[Pd].C(O)(C)C>[C:32]1([C:38]2[C:43]3[CH2:44][CH:45]([CH2:47][NH2:48])[O:46][C:42]=3[CH:41]=[CH:40][CH:39]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 33558AzideHCID 86599074(+/-)-(4-Phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 86599170(+/-)-(4-Phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl azide

Product 1

HCID 16226460(+)-1-(4-Phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamineYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

Treatment of (±)-(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.36 g, 3.57 mmol) with sodium azide (0.929 g, 14.29 mmol) generally according to the procedure described for intermediate 98 afforded (±)-(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl azide. The azide was dissolved in ethanol (50 mL) and palladium on carbon (0.083 g, 10 wt. %) was added and the reaction mixture was shaken under an H2 atmosphere (50 psi) for 6 h. The reaction mixture was filtered (celite) and the solvent removed in vacuo to provide a colorless oil. The oil was re-dissolved in isopropanol (3 mL) and hydrogen chloride (1.0 N in diethyl ether, 10.0 mL) was added. The resulting precipitate was filtered, washed (diethyl ether), and dried to afford 0.700 g (94%) of (±)-1-(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp 229-230° C.; Anal. calcd. for C15H15NOHCl: C, 68.83; H, 6.16; N, 5.35. Found: C, 66.11; H, 6.25; N, 5.02.

Workup

  1. filtrationThe reaction mixture was filtered (celite)
  2. customthe solvent removed in vacuo
  3. customto provide a colorless oil
  4. filtrationThe resulting precipitate was filtered
  5. washwashed (diethyl ether)
  6. customdried

Sources & evidence

ORD record
ord-df0fb4a49dc94d9f8e268b9d71f81e16
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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