ChemicalBook CAS DataBase List 3,4-dimethoxy-alpha-methylphenethylamine

3,4-dimethoxy-alpha-methylphenethylamine synthesis

12synthesis methods

Product Name:3,4-dimethoxy-alpha-methylphenethylamine
CAS Number:120-26-3
Molecular formula:C11H17NO2
Molecular Weight:195.26

776-99-8 Synthesis

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3,4-dimethoxy-alpha-methylphenethylamine

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Yield: 99%

Reaction Conditions:

Stage #1:3,4-dimethoxyphenylacetone with ammonium acetate;sodium acetate;sodium cyanoborohydride;acetic acid in methanol; pH=6 - 7 at 20; for 18 h;
Stage #2: with sodium hydroxide in methanol;water; pH=14

Steps:

36 Example 36. 2-(3,4-dimethoxy-phenyl)-1-methyl-ethylamine (3A)
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 x 30 mL of chloroform. Organic layers were combined, dried (Na2SO4) and concentrated under reduced pressure to give 2 g (10.24 mmol, 99%) of3A as a light yellow gum (M+H 196).

References:

Roche Diagnostics GmbH;F. Hoffmann-La Roche AG EP1498415, 2005, A1 Location in patent:Page 15; 31