Syntheses of Amine Derivatives of Phencyclidine

Article abstract of DOI:10.1021/jo00323a014

3-Aminophencyclidine (5) was synthesized by reduction of 3-nitrophencyclidine (3) using either H2 with Pd/C or Na2S in refluxing methanol.Attempts to isolate 4-aminophencyclidine (2), which we hoped to synthesize by hydrolysis of carbamate 15 which was isolated after reaction of amide 10 under Hofmann conditions employing bromine in CH3O(1-)/CH3OH at -40 deg C, were unsuccessful. 4-Aminomethylphencyclidine (18) was synthesized by LAH reduction of nitrile 13 as well as by reductive amination of aldehyde 20.Nitrile 13 and aldehyde 20 were synthesized from 4-bromophencyclidine (11) as was alcohol 26 which served as a precursor to 4-(2-aminoethyl)phencyclidine (19).Amine 19 was also synthesized by NaBH4 reduction of β-nitrostyrene 29 which was generated from aldehyde 20 by condensation with nitromethane using 1,5-diazabicycloundecene as the base catalyst followed by LAH reduction of resulting 4-(2-nitroethyl)phencyclidine (30).Mass spectra and ¹³C NMR spectra have been obtained on most of the phencyclidine derivatives.