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

HRID 1680876Notes

Reaction equation

HRID 1680876 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([CH3:16])([N+:13]([O-])=O)[CH3:12])=[CH:4][C:3]=2[O:2]1.C(O)(=O)C.COCCOC>[H][H].[Pt](=O)=O>[CH3:16][C:11]([NH2:13])([CH3:12])[CH2:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 80711,2-DimethoxyethaneHCID 23454854HCID 23454854, compound

Product 1

HCID 130205981-(2H-1,3-Benzodioxol-5-yl)-2-methylpropan-2-amineYield 72.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 0.8 g of 1-(3,4-methylenedioxyphenyl)-2-methyl-2-nitropropane, 100 mg of platinum dioxide, one ml of acetic acid and 20 ml of 1,2-dimethoxyethane is shaken at 60°-70° C. for 18 hours in hydrogen gas atmosphere under elevated pressure (initial pressure: 80 atmospheric pressures). After the reaction, the insoluble materials are removed by filtration, and the filtrate is evaporated to remove solvent. The residue is dissolved in ethyl acetate, and the solution is extracted with 5% hydrochloric acid. The extract is alkalized with potassium carbonate, and then extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and then evaporated to remove solvent. The residue (oil) is distilled at 100°-120° C. (bath temperature) under reduced pressure (0.04 mm Hg). 0.5 g of α,α-dimethyl-3,4-methylenedioxyphenethylamine are thereby obtained as an oil.

Workup

  1. customAfter the reaction
  2. customthe insoluble materials are removed by filtration
  3. customthe filtrate is evaporated
  4. customto remove solvent
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. extractionthe solution is extracted with 5% hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. washThe extract is washed with a saturated sodium chloride solution
  9. customdried
  10. customevaporated
  11. customto remove solvent
  12. distillationThe residue (oil) is distilled at 100°-120° C. (bath temperature) under reduced pressure (0.04 mm Hg)

Sources & evidence

ORD record
ord-77a001c3419d4ff29c5942eff6428b9c
Source dataset
uspto-grants-1981_06
Patent number
US04276304

Reaction notes

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