Hydrochloric Acid → (+-)-3,4-Dimethoxyamphetamine

HRID 325357

Reaction equation

HRID 325357 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([BH3-])#[N:16].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH2:16])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 698962-Propanone, 1-(3,4-dimethoxyphenyl)-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 8423(+-)-3,4-DimethoxyamphetamineYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3,4-dimethoxyphenylacetone (51.1 g., 0.26 m.) is dissolved in methanol (780 ml.), sodium cyanoborohydride (11.3 g., 0.18 m) is added and the mixture is stirred at room temperature for 67 hours. The reaction mixture is adjusted to pH 2 with concentrated HCl and the solvent is evaporated under reduced pressure. The residue is dissolved in H2O (250 ml.), the aqueous layer is extracted with ether (3×) and then rendered alkaline with KOH and extracted with CH2Cl2 (3×). After drying, the solvent is evaporated under reduced pressure and the product is distilled at 112°-5°/0.5 mm. to yield (VIII) (33.88 g., 67%).

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. dissolutionThe residue is dissolved in H2O (250 ml.)
  3. extractionthe aqueous layer is extracted with ether (3×)
  4. extractionextracted with CH2Cl2 (3×)
  5. customAfter drying
  6. customthe solvent is evaporated under reduced pressure
  7. distillationthe product is distilled at 112°-5°/0.5 mm

Sources & evidence

ORD record
ord-f82ea9512e454fe19c8b6291f86f5b76
Source dataset
uspto-grants-1984_04
Patent number
US04440774

Linked notes

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