Analgesics. I. N-Alkylated-1,2-diphenylethylamines Prepared by the Leuckart Reaction

Abstract

Vol. 68 containing 25 ml. of N-ethylmorpholine (total volume was 250 ml.) and 5 g. of a palladium charcoal catalyst containing 5% palladium were treated as aboye under an initial hydrogen pressure of 2500 pounds. Reduction was carried out at 175°, and the absorption of one mole of hydrogen required between ten and fifteeen hours. After removing the catalyst by filtration, ether was added to the solution which was then extracted with dilute hydrochloric acid to remove the N-ethylmorpholine. If this were not done, the solution turned dark because of the effect of the base on /J-tetralone. The clear, orange-yellow solution was washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure. Fifty grams of a fraction b. p. 116-135°at 5 mm. was obtained, and on shaking with a saturated sodium bisulfite solution gave 50 g. (40%) of the bisulfite addition compound of fl-tetralone. The ßtetralone recovered from several experiments was identified as its seinicarbazone m. p. 193-194°( reported m. p. 193°).8 SummaryThe preparation of /3-tetralone by the high pressure catalytic hydrogenation of /3-naphthol with a palladium catalyst is described.The mechanism of this reaction is briefly considered.

Ephenidine: A new psychoactive agent with ketamine-like NMDA receptor antagonist properties

“…Ephenidine appears in older chemical (Goodson et al., 1946) and pharmacological (Tainter et al., 1943) literature. In a brief medicinal chemistry report, relating it to MK-801 as an anticonvulsant, its affinity for the PCP binding site was given as 257 nM (Thurkauf et al., 1989) and information regarding its rapid metabolism has also recently appeared (Wink et al., 2014, Wink et al., 2015).…”

A STUDY OF THE WALLACH REACTION FOR ALKYLATION OF AMINES BY ACTION OF ALDEHYDES OR KETONES AND FORMIC ACID1

“…Formic acid functions chiefly as an aldehyde and appears to be the sole operative reducing agent in the reaction. 16 The acid character of formic acid is helpful to the extent that acid catalysis is involved, and perhaps as a solvent, but is otherwise obstructive.…”

“…Alkylation by the Wallach procedure tends to be exhaustive and is most useful for preparation of tertiary amines. The Leuckart procedure permits preparation of primary amines (from ammonium formate or formamide) or of secondary amines (from N-substituted formamides) (14,15,16), but preparation of tertiary amines from 13 Reports as to the utility of these suggestions are invited. N,N-disubstituted formamides requires the presence of formic acid (17).…”

New Biphenyl Derivatives I: 1 - (4-Biphenylyl) -2 -phenylethylamines as Potential Antispasmodic and Cardiovascular Agents

“…The self-association of the dihydroxy bile salts has been studied extensively (1)(2)(3)(4)(5). Most often, the association pattern has been interpreted in terms of a monomermicellar equilibrium model.…”

“…Although some investigators (1)(2)(3)(4)(5)(6)(7)(8) synthesized substituted I1 derivatives as possible analgesic agents, the 1biphenylyl or 2-biphenylyl analogs have not been prepared.…”