1-(4-Methoxyphenyl)-1-methylethyl azide → 2-(4-Methoxyphenyl)propan-2-amine

HRID 1940426Notes

Reaction equation

HRID 1940426 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([N:12]=[N+]=[N-])([CH3:11])[CH3:10])=[CH:5][CH:4]=1.[H][H]>CO.[Pt]=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH2:12])([CH3:10])[CH3:11])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 156972291-(4-Methoxyphenyl)-1-methylethyl azideHCID 178418361HCID 178418361, compound

Product 1

HCID 110082782-(4-Methoxyphenyl)propan-2-amineYield 95%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

1.58 g of platinum oxide were added to a solution of 21.0 g of 1-(4-methoxyphenyl)-1-methylethyl azide [prepared as described in step (a) above] in 100 ml of methanol. The reaction mixture was then stirred for 5 hours under a stream of hydrogen. At the end of this time, the mixture was filtered, diluted with methylene chloride, and washed with an aqueous solution of sodium hydrogencarbonate, with water and with a saturated aqueous solution of sodium chloride, in that order. It was then dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure, to give 17.2 g (yield 95%) of the title compound.

Workup

  1. filtrationAt the end of this time, the mixture was filtered
  2. additiondiluted with methylene chloride
  3. washwashed with an aqueous solution of sodium hydrogencarbonate, with water and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialIt was then dried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-1dfccbeb4e4f47af85ed2b98139b0cab
Source dataset
uspto-grants-1997_12
Patent number
US05698720

Reaction notes

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