Phenethylamine Patents

US patents found in class 564 subclass 381 on phenethylamines with alpha alkyl substituents and subclass 382 on phenethylamines with beta alkyl substituents. Sometimes the alpha and beta positions get confused and also the patents tend to disclose both so they have been grouped together here.

1879003 inventor: Gorden Alles, benzaldehyde + EtNO2 -> phenylnitropropene which is reduced electrolytically or using Na(Hg) in CH3COOH or EtOH

1921424 oxime of dibenzyl ketone made from dibenzyl ketone and hydroxylamine and reduced using Na and alcohol

2011790 p-MeO-P2P aminated with MeNH3Cl + NaOOCH (example 4)

2146473 N-methylation using H2CO + activated Al turnings

2205530 2MeO-P2P, activated Al turnings, ether, 40% MeNH2 refluxed 6 hours

2246529 xylyl methyl ketone aminated with H2NCOH 165-170º, can include one mole of HCOOH

2278373 carbonyl + NH3 + H2 --> RNH2, secondary or tertiary ROH better than primary ROH

2361372 m-CH30-phenylnitropropene electrolytic reduction

2378889 demethylation of N-alkyl-DMA using 48% HBr, 4 hrs.

2382686 4Me-P2P from Me-C6H6CH2CN + EtOAc using Na in EtOH, 4Me-P2P aminated with MeNH2 using Ni catalyst and H2 at several atmospheres and 90-100º C

2396580 eugenol, etc. + 60% HBr --> alkyl bromide which is aminated with NH3 in ETOH (example 2)

2507468 phenylisopropylamine phosphate

2597446 p-MeO-P2Pol (from p-MeO-C6H6CHO) --> propenyl benzene using H2SO4 on vermiculite

2647930 catalytic reduction of nitroolefins

3078307 includes reduction of phenylnitropropenes with LiAlH

3117160 reduction of nitroolefins

3152173 P2P, alpha-halo propiophenone, C6H6COCOCH3 (diketone)

3187046 hydrogenation of nitroolefins --> oximes <--> ketone and NH3

3187047 hydrogenation of ketones with NH3, RCOOH, Raney Ni: 2,5-DMA example

3198833 prior art P2P oximes reduced to amines: P2Pol --> P2P ; little detail

3237528 N-phenylethyl piperazines

3485874 ortho and para Br phenylisopropylmethylamines

3536712 ring bromination in CH3COOH, example 1

3547999 inventor: Alexander Shulgin, phenylethylamines with MeO, EtO, PrO, Me, etc.substituents

3655737 phenyl nitropropenes including reaction with Fe + HCl --> ketone (no example given)

3657244 cathinones reduction to ephedrine, reaction of epoxide with RNH2 --> ephedrine

3689504 N-alkyl MDA

3929871 nitropropene --> ketone, example 1

4105695 ring bromination (example 5), also alkyl thio compounds such as 1-(2,5-dimethoxy 4 methyl thio phenyl) 2 amino butane

4277420 ephedrine and pseudoephedrine, cathinone hydrogenated to the phenethylamine (no example reactions), phenyl 1,2-propanedione and 2 oxime

5220068 1,3-diphenylacetone (example 5), 96% EtOH, n-propylamine, Al foils(Hg)


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