HCID 19064690, compound → HCID 19064534, compound

HRID 481975Notes

Reaction equation

HRID 481975 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([CH3:12])=[C:9]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[C:8]=2[CH:18]=1)([O-])=O.[H][H]>[Pt].O1CCCC1>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([CH3:12])=[C:9]([CH2:13][CH2:14][N:15]([CH3:16])[CH3:17])[C:8]=2[CH:18]=1

Participants

5

Reactant 2

HCID 19064690HCID 19064690, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19064534HCID 19064534, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.1 gm (8.6 mMol) 5-nitro-2-methyl-3-(N,N-dimethyl-2-aminoethyl)benzofuran and 0.5 gm platinum on carbon in tetrahydrofuran was hydrogenated at an initial hydrogen pressure of 60 p.s.i. at room temperature for 15 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residual oil was subjected to flash silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure to provide 1.42 gm (76%) 5-amino-2-methyl-3-(N,N-dimethyl-2-aminoethyl)benzofuran. The dihydrochloride salt was prepared and recovered as a light brown solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. washeluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide
  4. additionFractions containing product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-54b73c05167c4e91bc4fa53073df3500
Source dataset
uspto-grants-1998_08
Patent number
US05792763

Reaction notes

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