Methane → 1-(2H-1,3-Benzodioxol-5-yl)-2-methylpropan-2-amine

HRID 616258Notes

Reaction equation

HRID 616258 reaction equation
[CH3:1][C:2]([N+:15]([O-])=O)([CH3:14])[CH:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1.C([O-])(=O)C.[Na+].C.[H][H]>C(O)(=O)C.[Pt]=O>[CH3:14][C:2]([NH2:15])([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 517045Sodium AcetateHCID 234548395-(1-Chloro-2-methyl-2-nitropropyl)-2H-1,3-benzodioxoleHCID 178418361HCID 178418361, compound

Product 1

HCID 130205981-(2H-1,3-Benzodioxol-5-yl)-2-methylpropan-2-amine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 51.52 g (0.2 mole) of 1,1-dimethyl-2-chloro-2-(3,4-methylenedioxyphenyl)nitroethane, 2.0 g of 83.8 weight % purity platinum oxide, 18.0 g (0.22 mole) of sodium acetate and 4.0 g of "Darco" in 96 ml of acetic acid and 500 ml of SDA-30 was stirred under a hydrogen atmosphere at 1000 p.s.i. and 100° C for a period of 5 hours, after which uptake of hydrogen ceased. The solution was cooled and filtered, and the filtrate was concentrated to an oil which was treated with 400 ml of water. The mixture was extracted twice with ether, after which the aqueous layer was made alkaline by addition of 20% aqueous sodium hydroxide and extracted four times with chloroform. The combined extracts were filtered through "Dicalite" (Trade Mark), washed with water, dried and concentrated to a light yellow oil which was distilled using a 2" 19.38 distillation column to give 1,1-dimethyl-2-(3,4-methylenedioxyphenyl)ethylamine as a clear colourless oil, b.p. 68°-85° C, 0.06-0.04 mm Hg (Yield 24.4 g, 63.2%)

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated to an oil which
  4. additionwas treated with 400 ml of water
  5. extractionThe mixture was extracted twice with ether
  6. additionby addition of 20% aqueous sodium hydroxide
  7. extractionextracted four times with chloroform
  8. filtrationThe combined extracts were filtered through "Dicalite" (Trade Mark)
  9. washwashed with water
  10. customdried
  11. concentrationconcentrated to a light yellow oil which
  12. distillationwas distilled
  13. distillationa 2" 19.38 distillation column

Sources & evidence

ORD record
ord-58e9a8a5dff44a33b9c551c0dddb7695
Source dataset
uspto-grants-1978_02
Patent number
US04073798

Reaction notes

Loading…