1.1- Diphenyl-propylamine

Prenyl amine (66) was long used in the treatment of angina pectoris, in which condition it was believed to act by inhibiting the uptake and storage of catecholamines in heart tissue. Droprenilamine (69), an analogue in which the phenyl ring is reduced, acts as a coronary vasodilator. One of several syntheses involves simple reductive alkylation of 1,1-diphenyl-propylamine (67) with cyclohexyl acetone (68)... 

Chemical Name 7-phenyl-N-( TphenylethyDbenzenepropanamine hydrochloride Common Name N-(1-phenylethyl)-3,3-diphenyl-propylamine... 

PAJ Janssen Synthetic Analgetics, Parti, Diphenyl-propylamines, Pergamon Press, New York (1960). 

Propanol with magnesium in reduction of chlorobenzene, 47, 104 Propionyl fluoride, 46, 6 n Propylamine, 46, 85 n Propylhydrazine, 46, 85 C ( Propyl) N phenylmtrone, genera tion from phenylhydroxylamme and n butyraldehyde, 46, 97 Purification of tetrahydrofuran (Warning), 46,105 4H Pyran 4-one, 2 6 dimethyl 3,5 diphenyl, 47, 54... 

The triplet reaction of 2-nitrodibenzo[fc,primary amines (n-propylamine and benzylamine) was studied110 in polar and apolar solvents. In polar solvents, the irradiation results in the formation of two isomeric compounds, (alky-lamino)hydroxynitrodiphenyl ether andiV-(alkylamino)-2-nitrophenoxazine (equation 54). In apolar solvents, only the nitrophenoxazine is obtained. In polar solvents, the exciplex formed between the 2-n i trodi benzol h,e [ 1,4]dioxin triplet state and amines dissociates to the solvated radical ions, from which the diphenyl ether arises. 1-Nitrodibenzo[fr,e][l,4]dioxin is stable even on prolonged irradiation. 

As noted earlier, most classical antidepressant agents consist of propylamine derivatives of tricyclic aromatic compounds. The antidepressant molecule tametraline is thus notable in that it is built on a bicyclic nucleus that directly carries the amine substituent. Reaction of 4-phenyl-l-tetralone (18) (obtainable by Friedel-Crafts cyclization of 4,4-diphenyl butyric acid) with methyl amine in the presence of titanium chloride gives the corresponding Schiff base. Reduction by means of sodium borohydride affords the secondary amine as a mixture of cis (21) and trans (20) isomers. The latter is separated to afford the more active antidepressant of the pair, tametraline (20). 

Dimethylaminovinyl)-5-oxo-2,7-diphenyl-5//-pyrano 4,3-/ pyridine-3-car-bonitrile (43) with propylamine gave 8-oxo-l-phenacyl-3-phenyl-7-propyl-2,7-naphthyridine-4-carbonitrile (44) (PrNH2, pyridine, reflux 58%).987... 

Isothiazole gave a low yield of thiazole on irradiation in propylamine, but the reverse reaction was not observed.149 Phenyl- and diphenyl-isothiazoles gave thiazoles on irradiation,150 and the reverse reactions have also been reported.84,151 It appears likely that isothiazole-thiazole photorearrangements proceed through a common intermediate, possibly a tricyclic species in which the negative charge is stabilized by resonance with the phenyl group (Scheme 42).80,150... 

Solasulfoae. i,I - Sulfonylbis(4,l-phenyleneimi-no)]bisf3-phenyl-l,3-propanedisu fonic acid] tetrasodium salt di(>-phenyl propylamine)-4,4 -diphenyl sulfone a,a, -y,y -sodium tetrasulfonate tetrasodium 4,4 -bistv-phenyl -... 

A mixture of 3,4-diphenyl-4-oxazolin-2-one and -propylamine refluxed 14hrs. 5-hydroxy-3,4-diphenyl-l- -propylimidazolidin-2-one (Y 94%) dissolved in 95%-ethanol, treated at 50° with coned. H2SO4, allowed to stand 2hrs. at room temp., then coned, to 1/3 of the original volume -> 3,4-diphenyl-l- -propyl-4-imidazolin-2-one (Y 85%). F. e. s. M. F. Saettone and V. Nuti, J. Pharm. Sci. 57, 1798 (1968). 

Preliminary observations on the photochemical behaviour of isothiazoles have been briefly reported. The parent base is partially converted into thiazole on irradiation (7% in propylamine, 1% in ether), several unidentified products being formed (15%) side by side. 3-Phenyl- and 3,5-diphenyl-isothiazole are converted into 4-phenyl- (12%) and 2,4-diphenyl-thiazole (48%), respectively, but 5-phenylisothiazole preserves its ring system, merely producing small quantities (2.3%) of the 3-phenyl isomer. The reactions are believed to proceed by way of tricyclic sulphonium cations of the type previously postulated by Kojima and Maeda. It is recalled that the reverse photoisomerization is also on record (see syntheses, above). 

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