2-Propanone, 1-(3,4-dimethoxyphenyl)- → (+-)-3,4-Dimethoxyamphetamine

HRID 2099723Notes

Reaction equation

HRID 2099723 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](=O)[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([O-])(=O)C.[NH4+].C([O-])(=O)C.[Na+].C([BH3-])#[N:26].[Na+]>C(O)(=O)C.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH2:26])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 698962-Propanone, 1-(3,4-dimethoxyphenyl)-HCID 517045Sodium AcetateHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 8423(+-)-3,4-DimethoxyamphetamineYield 99.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To 2 g (10.29 mmol) of 3,4-dimethoxyphenyl acetone was added 10 mL of methanol, 7.9 g (102 mmol) of ammonium acetate, 844 mg (10.2 mmol) of sodium acetate and 970 mg (15.4 mmol) of sodium cyanoborohydride. The pH of the reaction was adjusted to between 6-7 by addition of glacial acetic acid. The reaction mixture was allowed to stir at room temperature 18 hours and concentrated under reduced pressure. To the residue 100 mL of water was added, and the pH of the reaction was adjusted to 14 using 6 N NaOH. The aqueous layer was extracted with 6×30 mL of chloroform. Organic layers were combined, dried (Na2SO4) and concentrated under reduced pressure to give 2 g (10.24 mmol, 99%) of 3A as a light yellow gum (M+H 196).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue 100 mL of water was added
  3. extractionThe aqueous layer was extracted with 6×30 mL of chloroform
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bfe32e40abd8429d9f6d4c5d97dbc94a
Source dataset
uspto-grants-2009_08
Patent number
US07569676B2

Reaction notes

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