Author Topic: 3,4-dimethoxy-5-methylphenethylamine  (Read 570 times)

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Vitus_Verdegast

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3,4-dimethoxy-5-methylphenethylamine
« on: April 10, 2003, 10:35:00 PM »
Preparation of 5-desoxy-mescaline :


beta-(3,4-dimethoxy-5-methylphenyl)ethylamine


Taken from Arch. Pharm. 1963, p. 656 :

Clemmensen reduction of o-vanillin gives 40% yield of 2-hydroxy-3-methoxytoluene according to Ber. D. Chem. Gesell. 49 (1916) p. 1488

3-methoxy-4-hydroxy-5-methylbenzyl alcohol

6.9 gr (0.05 mol) 2-hydroxy-3-methoxytoluene, obtained from Clemmensen reduction of o-vanillin, was dissolved with 3 gr (0.053 mol) KOH in 16 ml water, and 4.3 gr (0.05 mol) 35% formaldehyde solution was added and the mixture was stirred at 40-50° for 4 hours. The green colour of the mixture became an intensive violet. After cooling the mixture was slightly acidified with 1% HCl and extracted with ether. The solvent was evaporated and the resulting oil recrystallised from EtOAc. This was purified by means of column chromatography with a silica gel column and chloroform as the eluting solvent. Next to tars and a bit of unchanged precursor there was obtained 10% 3,3'-dimethoxy-4,4'-dihydroxy-5,5'-dimethyldiphenylmethane (mp. 129-130°) and 4.1 gr (49%) 3-methoxy-4-hydroxy-5-methylbenzyl alcohol, mp. 81°


3,4-dimethoxy-5-methyl-benzyl alcohol

5.5 gr 3-methoxy-4-hydroxy-5-methylbenzyl alcohol was dissolved in methanol and treated with an ethereal diazomethane solution. After work-up the phenol-free yellow oil was distilled at the Kugelrohr (120-125°/1mm), yield 5 gr (84%).


3,4-dimethoxy-5-methyl-benzyl chloride

5 gr 3,4-dimethoxy-5-methyl-benzyl alcohol was dissolved in 40 ml anhydrous ether and placed in an ice-bath. The mixture was saturated with dry HCl-gas. After evaporation of the solvent there remained an colourless oil, which was distilled at the Kugelrohr (105-110°/3mm), yield 5 gr (91%)


3,4-dimethoxy-5-methyl-benzyl cyanide

5 gr 3,4-dimethoxy-5-methyl-benzyl chloride was dissolved in 5 gr DMF and heated with stirring to 70-75°, and a solution of 1.5 gr NaCN, 4 drops of water and 5 gr DMF was added dropwise. The mixture was left stirring for 3 hours at 70-75°, solvent was evaporated and the resulting oil was distilled at the Kugelrohr (115°/1mm). Yield 3.3 gr (70%).


beta-(3,4-dimethoxy-5-methylphenyl)ethylamine

To a suspension of 1.6 gr (0.04 mol) LiAlH4 in 50 ml anhydrous ether was gently added with good stirring a solution of 5.2 gr (0.04 mol) anhydrous AlCl3 in 60 ml anhydrous ether, followed by the dropwise addition of 3.8 gr (0.02 mol) 3,4-dimethoxy-5-methyl-benzyl cyanide. There was a vigorous reaction and a white solid precipitated. The mixture was stirred for an additional hour at RT. After work-up 3.0 gr (77%) of a brown oil was obtained, this was made into the HCl salt and recrystallised from MeOH and ether, mp. 208°

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Chimimanie

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great vitus!
« Reply #1 on: April 10, 2003, 11:30:00 PM »
very interesting!

That is a really nice thing, i hope i will have the luck to eat some meta-desoxy mescaline one day....