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

HRID 1828983Notes

Reaction equation

HRID 1828983 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-338c120e9bf24a03a3e39a3ea9bce53c
Source dataset
uspto-grants-2006_06
Patent number
US07060847B2

Reaction notes

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