Acetic Acid → 1-(4-Methoxyphenyl)-2-methylpropan-2-amine--hydrogen chloride (1/1)

HRID 1680867Notes

Reaction equation

HRID 1680867 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([Cl:16])[C:10]([CH3:15])([N+:12]([O-])=O)[CH3:11])=[CH:5][CH:4]=1.C(O)(=O)C.COCCOC>[H][H].[Pt](=O)=O>[ClH:16].[CH3:15][C:10]([NH2:12])([CH3:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 80711,2-DimethoxyethaneHCID 13020596HCID 13020596, compound

Product 1

HCID 918911-(4-Methoxyphenyl)-2-methylpropan-2-amine--hydrogen chloride (1/1)Yield 55.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 812 mg of 1-(4-methoxyphenyl)-1-chloro-2-methyl-2-nitropropane, 2 ml of acetic acid, 150 mg of platinum dioxide and 20 ml of 1,2-dimethoxyethane is stirred at 20° C. for 2 hours in hydrogen gas atmosphere under 70 atmospheres, and then at 45° C. for 4.5 hours under 68-65 atmospheres, and then at 80° C. for 14 hours under 68 atmospheres. After cooling, the reaction mixture is filtered to remove insoluble materials, and said insoluble materials are washed with ethanol and water, successively. The filtrate and the washing are combined, and the combined solution is evaporated to remove solvent. Cold 10% hydrochloric acid is added to the residue (brown oil), and the mixture is extracted with chloroform. The aqueous layer is alkalized with 10% sodium hydroxide under cooling, and then extracted with benzene. The extract is washed with water and a saturated sodium chloride solution, successively. The washed extract is dried and then evaporated to remove solvent. The residue (colorless oil, 460 mg) is dissolved in 2 ml of isopropylalcohol. 4 ml of ether containing hydrogen chloride (27 g/500 ml) are added to the isopropylalcohol solution, and said solution is allowed to stand. The crystalline precipitates are collected by filtration, washed with ether, and then recrystallized from isopropylalcohol. 400 mg of α,α-dimethyl-4-methoxyphenethylamine hydrochloride are thereby obtained as colorless plates.

Workup

  1. waitat 80° C. for 14 hours under 68 atmospheres
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. customto remove insoluble materials
  5. washare washed with ethanol and water
  6. customthe combined solution is evaporated
  7. customto remove solvent
  8. additionCold 10% hydrochloric acid is added to the residue (brown oil)
  9. extractionthe mixture is extracted with chloroform
  10. temperatureunder cooling
  11. extractionextracted with benzene
  12. washThe extract is washed with water
  13. extractionThe washed extract
  14. customis dried
  15. customevaporated
  16. customto remove solvent
  17. dissolutionThe residue (colorless oil, 460 mg) is dissolved in 2 ml of isopropylalcohol
  18. addition4 ml of ether containing hydrogen chloride (27 g/500 ml)
  19. additionare added to the isopropylalcohol solution
  20. customThe crystalline precipitates
  21. filtrationare collected by filtration
  22. washwashed with ether
  23. customrecrystallized from isopropylalcohol

Sources & evidence

ORD record
ord-f1217b91148d49b2b86efcb804bdce1c
Source dataset
uspto-grants-1981_06
Patent number
US04276304

Reaction notes

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