P-Phenethylamine

Synthesis of Alkviamines. General Procedures. Method (A). The synthesis of p-phenethylamine is representative. A flame dried, nitrogen-flushed, 100 ml flask, equipped with a septum inlet, magnetic stirring bar and reflux condenser ivas cooled to 0°C. Sodium borohydride (9.5 mmol, 0.36 g) was placed in the flask followed by sequential addition of THF (13-15 ml) and BF3-Et20 (12 mmol, 1.5 ml) at 0°C. After the addition, the ice bath was removed and the contents were stirred at room temperature for 15 min. The solution... 

Huang, J.T., and Ho, B.T. The effect of pretreatment with iproniazid on the behavioral activities of P-phenethylamine in rats. 

A rather complex fused isoindoline (87) has been found to show good anorectic activity. This substance differs from other anorectic agents by not being a p-phenethylamine analogue. Preparation of this compound starts by reaction of a substituted benzoyl-benzoic acid (82) with ethylene diamine. The product (84) can be rationalized as being the aminal from the initially obtained monoamide 83. This is then subjected to reduction with lithium aluminum hydride... 

B. a,a-Dimethyl-p-phenethylamine. In a 3-1., three-necked, round-bottomed flask equipped with a reflux condenser and a sealed stirrer are placed 246 g. (1.39 moles) of N-formyl-a,a-dimethyl-d-phenethylamine and 2.11. of 20% sodium hydroxide solution. The mixture is heated under reflux with vigorous stirring for 2.5 hours or until a test portion of the oily layer dissolves completely in cold 5% hydrochloric acid. The reaction mixture is cooled, 750 ml. of benzene is added, the mixture is stirred, and the benzene layer is separated. The benzene solution is shaken with a saturated sodium chloride solution, the benzene removed... 

Finally, attachment of a rather complex side chain to the para position of the benzene ring on the sulfonamide leads to the very potent, long-acting oral antidiabetic agent, glyburide (215). Preparation of this compound starts with the chlorosul-fonation of the acetamide of P-phenethylamine (209). The resulting sulfonyl chloride (210) is then converted to the sulfonamide (211) and deacylated (212). Reaction with the salicylic acid derivative, 213, in the presence of carbodiimide affords the amide, 214. Condensation of that with cyclohexylisocyanate affords glyburide (215). ... 

Chemical Name 3,4-Dihydroxy-N-[3-(4-hydroxyphenyl)-l-methylpropyl]-p-phenethylamine... 

The cold solution was then allowed to stand overnight and all crystalline material filtered through a sintered glass filter. The filtrate was treated with an additional 300 ml of concentrated hydrochloric acid to yield a heavy white precipitate. The precipitate was filtered, dried and combined with the initial precipitate obtained as described above. The combined precipitated product, 3,4-dihydroxy-N-[3-(4-hydroxyphenyl)-l-methyl-n-propyl-p-phenethylamine hydrochloride, had a melting point of about 184°C to 186°C after recrystallization from boiling 4 N hydrochloric acid. 

The hydrogenation of P-nitrostyrenes to P-phenethylamines can be accomplished over palladium catalyst in strongly acidic conditions.49-51 Kindler et al. hydrogenated P-nitrostyrene to 2-phenethylamine in 84% yield over a palladium black in acetic acid-sulfuric acid (eq. 9.26).49 In the absence of sulfuric acid the uptake of the same amount of hydrogen required a much longer time and the phenethylamine was obtained in only slight amounts. 

DIMETHOXY-P-PHENETHYLAMINE see DOE200 4-(2,5-DIMETHOXYPHENETHYL)ANILINE see DON400... 

Chen et al. reported a more environmentally friendly version of the Pictet-Spengler reaction <06H1651>. In this report, a series of 2-phenylsulfonyl-l,2,3,4-tetrahydroisoquinoline-1-carboxylic acid ethyl ester derivatives 114 were synthesized in good yields through the cyclization of A-phenylsulfonyl-P-phenethylamines 115 with a-acyl sulfide 116 using phenyliodine(III) bis(trifluoroacetate) (PIFA) in ionic liquid ([bminjPFJ. The use of the ionic liquid allows for a simple purification and [bmin]PF can conveniently be recycled. 

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