3-Benzyl-4-phenyl- -Hydrochlorid

This approach (Scheme 3) has been applied (53JCS1636) to the synthesis of 4(5)-aminoimidazole derivatives with potential antihistamine or anthelmintic properties. For example, 4(5)-amino-2-thymyloxymethylimidazole (47) was obtained from benzyl-thymyloxy acetothioimidate hydrochloride (42) (75%). Similarly, 4(5)-amino-2-phenylimidazole (48) and 4(5)-amino-2-(thiophen-3-yl)imidazole (49) were prepared (72CA19645) from benzyl-phenyl acetothioimidate hydrochloride (43) and benzyl-(thiophen-3-yl) acetothioimidate hydrochloride (44), respectively. 

N-(2-Amino-ethyl)-0-(2-phenyl-ethyl)- E16a, 274 (N-Alkyl./ NH2-Dephosphorylier.) N-(3-Amino-propyl)-0-benzyl- -Bis-Hydrochlorid E16a, 273 (NH2-Deacylier.)... 

SYNS EPHETONIN EPHETONINE dl-a-(l-(METHYLAMINO)ETHYX) BENZYL ALCOHOL HYDROCHLORIDE 1-PHENYL-2-METHYL-AMINOPROPANOL-1 ILACEPHEDRINE HYDROCHLORIDE... 

SYNS a-(l-AMINOETHYL)BENZENEMETHANOL HYDROCHLORIDE a-(l-AMINOETHYL)BENZYL ALCOHOL HYDROCHLORIDE ( )-2-AMINO-l-PHENYL-l-PROPANOL HYDROCHLORIDE O-HYDROXY-P-AMINOPROPYLBENZENE HYDROCHLORIDE MONHYDRIN MUCORAMA MYDRIATINE dl-NOREPHEDRINE HYDROCHLORIDE dl-l-PHENYL-2-AMINO-l-PROPANOL MONOHYDROCHLORIDE PHENYLPROPANOLAMINE HYDROCHLORIDE... 

The benzene was distilled from the extract and the residue of d-N-methyl-N-benzyl-)3-phenyl-isopropylamine was distilled at reduced pressure. The thus obtained free base, distilling at 127°C at a pressure of 0.2 mm of mercury and having an np of 1.5515, was dissolved in ethyl acetate and a molar equivalent of ethanolic hydrogen chloride was added thereto. Anhydrous ether was added to the mixture and d-N-methyl-N-benzyl-)3-phenylisopropyl-amine hydrochloride precipitated from the reaction mixture as an oil which was crystallized from ethyl acetate to give crystals melting at 129° to 130°C. 

Benzyl cyanide is first reacted with 2-butylbromide in the presence of sodium amide to give 2-phenyl-3-methylvaleronitrile which is hydrolyzed by sulfuric acid to give 3-methyl-2-phenyl-pentanoic acid. 24 g of 2-phenyl-3-methyl-pentanoic acid are heated for one hour at 175° to 185°C with 30 g of 2-diethylaminoethanol and 0.5 g of sodium methylate. The excess diethyl-aminoethanol is removed in vacuo, the residue is dissolved in 300 cc of 2 N-acetic acid, the acid solution is shaken with ether and made alkaline with concentrated potassium carbonate solution and ice. The ether solution Is washed with water, dried with sodium sulfate and evaporated. The residue is distilled under high vacuum, yielding 20 to 21 g of the basic ester (60% of the theoretical) is obtained, the ester boiling at 98° to 100°C at a pressure of 0.03 mm. The hydrochloride of the ester melts at 112° to 113°C and the methobromide at 100° to 101°C. 

Athyl-benzyl-amin — Athyl-(2-phenyl-dthyl)-amin —> Athyl-(2,2-diphenyl-dthyl)-amin — Athyl-(2,2-dimelhyl-propyl)-amin-Hydrochlorid... 

Lack of selectivity in the reaction of the /3-D-glucoside derivative with one molar equivalent of benzylthiocarbonyl chloride has also been noted 40% of the 2,3-diester and 40% of the starting material were isolated.40 Similarly, unimolar benzoylation of phenyl 4,6-0-benzylidene-/3-D-glucopyranoside gave only 9% of the 3-ester, together with 47% of the 2,3-diester.41 Acylation of benzyl 4,6-0-benzylidene-/8-D-glucopyranoside with acetic anhydride-pyridine-pyridine hydrochloride yielded,42 in contrast to the reaction with the... 

In analoger Weise lassen sich konfigurativ einheitliche, 2-substituierte 1-Amino-cy-clohexan-Hydrochloride herstellen. Man erhiilt so in ahnlich hohen Ausbeuten und mit hohen ee-Werten die Hydrochloride von optisch-aktivem 2-Amino-1-methyl-, 2-Amino-1-ethyl-, 2-Amino-1-benzyl- und 2-Amino-l-phenyl-cyclohexan2. 

Durch Reaktion von Cyclohexyl-dichlor-boran mit Azido-phenyl-methan, 4-Azido-l-bu-ten bzw. 4-Azido-l-butin und anschlieBende Methanolyse erhalt man Benzyl-cyclohexyl-amin (88%), 4-Cyclohexylamino-l-buten (78%) bzw. 4-Cyclohexylamino-l-butin (80%) (als Hydrochloride)2 ... 

Phenylacetamide has been obtained by a wide variety of reactions from benzyl cyanide with water at 250-260° 6 from benzyl cyanide with water and cadmium oxide at 240° 6 from benzyl cyanide with sulfuric acid 7 8 by saturation of an acetone solution of benzyl cyanide with potassium hydrosulfide 9 from benzyl cyanide with sodium peroxide 10 by electrolytic reduction of benzyl cyanide in sodium hydroxide 11 from ethyl phenyl-acetate with alcoholic 12 or aqueous 13 ammonia from phenyl-acetic acid with ammonium acetate 14 or urea 15 from diazoacetophenone with ammoniacal silver solution 16 from phenyl-acetic acid imino ether hydrochloride and water 17 from acetophenone with ammonium poly sulfide at 215° 18 from benzoic acid 19 and by heating the ammonium salt of phenyl-acetic acid.20... 

Meperidine hydrochloride (the full name) is a synthetic opioid. It is synthesized by the reaction of chemicals not found in opium. Specifically, meperidine hydrochloride is produced by the reaction of dichlorodi-ethyl methylamine with benzyl cyanide, to produce ethyl l-methyl-4-phenyl-isonipecotate hydrochloride (meperidine s chemical name). Some references to meperidine classify it as a totally synthetic opioid. Semi-synthetic opioids are produced by using one of the opiates as a starting material. Two examples of semi-synthetic opioids are hydrocodone and heroin. Hydrocodone is produced by the chemical modification of codeine, while heroin is made by chemically altering morphine. 

A-Methyl-4-phenyl-l,2,3,6-tetrahydropyridine (MPTP, 92) injected in small amounts to man and other primates produce a clinical and neurochemical state similar to Parkinson s disease1"9,110. An analog of MPTP, 0-fluoromethyl-MPTP, 93, has been labelled with 18F1U by benzyl halide substitution on o-(chloromethyl)-MPTP hydrochloride or the corresponding brominated compound with [18F]fluoride in dry MeCN, to study the behaviour of MPTP in animal brains using PET. 

Other Organic Compounds aniline hydrochloride benzyl hydroperoxide butyl chloride dicyclohexyl peroxide diethyl sulfide methyl iodide 2-naphthoyl bromide sodium S-phenyl thiosulfite fert-butyl fluoride... 

Aniline hydrochloride Benzyl hydroperoxide Butyl chloride Dicyclohexyl peroxide Diethyl sulfide Methyl iodide 2-Naphthoyl bromide Sodium S-phenyl thiosulfite ferf-Butyl fluoride... 

Rather less common are condensations between a-hydroxyketones, ammonia and an imidate. Equivalent amounts of the hydrochloride salt of the imidate and the or-substituted carbonyl compound (cr-halogeno-and a-acetoxyketones also take part) are heated (40-70°C) in liquid ammonia (3-48 h) at elevated pressures. Yields of imidazoles vary between 10 and 90%, but the requirements of working with liquid anomonia in an autoclave may make this approach unappealing if alternatives are available [42,43]. Examples include 4-hydroxymethyl- (35%), 4-hydroxymethyl-2-phenyl- (73%), 4-hydroxymethyl-2-(p-tolyl)- (68%) and 2-benzyl-4-hydroxymethylimidazoles (85%) [44]. 

---