------------------------------------------------------------------------------- Propiophenones to amphetamines ------------------------------------------------------------------------------- Drone 342: The following is the product of my strip-mining of Beilstein. Unfortunately, the list was more extensive, with far more goodies in the original version, but it got lost and this is take 2. This is a really interesting method, since propiophenone is a very cheap, very industrial chemical. Propiophenones are easilt made with propionic acid, polyphosphoric acid, and any number of substituted benzenes -- 2,5-dimethoxypropiophenone's synth is listed in PiHKAL using this method. This would be an excellent means of producing the "DO" series (definately not my ally, but some people love 'em), as well as plenty of other ethereal delights. The first reaction citations are propiophenones reacting with alkyl nitrites, follwoed by the reduction to amphetamine. The interesting part of this, in my ponion, is the *other* reactions involving the PhCO(C=NOH)Me intermediate -- cyclizations for synthesizing a galaxy of bizarre rigid-bodied and polycyclic analogs -- all uncharted territory in methylenedioxyland (indanes aside.) If there's any need for more information, there's dozens more reactions where these came from detailing even more about these little chemical anomolies. BTW, I got the JMC article you were talking about -- 33; 2; 1990; 703-710. Actually, I already had this one, but hadn't remembered the chemical similarity. -drone #342 Reaction Reaction ID 724478 Reactant BRN 606215 1-phenyl-propan-1-one 1701036 nitrous acid butyl ester Product BRN 509304 1-phenyl-propane-1,2-dione 2-oxime ------------------------- Reaction Details Reaction Classification Preparation Reagent hydrogen chloride diethyl ether Ref. 1 1795343; Journal; Hartung; ORSYAT; Org.Synth.; 16; 1936; 46; Ref. 2 1795341; Journal; Hartung; JACSAT; J.Amer.Chem.Soc.; 51; 1929; 2264; Reaction Reaction ID 724534 Reactant BRN 606215 1-phenyl-propan-1-one 969510 3-methyl-1-nitrosooxy-butane Product BRN 1908501 2--1-phenyl-propanone-(1) ------------------------- Reaction Details Reaction Classification Preparation Ref. 1 1821372; Journal; Recl.Trav.Chim.Pays-Bas; 57; 1938; 133, 142; Ref. 2 1821370; Journal; Gazz.Chim.Ital.; 60; 1930; 866, 869; Reaction Reaction ID 724536 Reactant BRN 606215 1-phenyl-propan-1-one 969510 3-methyl-1-nitrosooxy-butane Product BRN 509304 1-phenyl-propane-1,2-dione 2-oxime ------------------------- Reaction Details Reaction Classification Preparation Reagent hydrochloric acid Ref. 1 1778601; Journal; Claisen; Manasse; CHBEAM; Chem.Ber.; 22; 1889; 529; Reaction Reaction ID 724548 Reactant BRN 606215 1-phenyl-propan-1-one Product BRN 1908501 2--1-phenyl-propanone-(1) ------------------------- Reaction Details Reaction Classification Preparation Reagent NaCl concentrated aqueous hydrochloric acid isopropyl alcohol NaNO2 Other conditions weiteres Reagens: konz. Schwefelsaeure Ref. 1 1821373; Patent; Sharp & Dohme Inc.; US 2248035; 1938; Reaction Reaction ID 1319864 Reactant BRN 606215 1-phenyl-propan-1-one Product BRN 509304 1-phenyl-propane-1,2-dione 2-oxime ------------------------- Reaction Details 1 of 3 Reaction Classification Preparation Reagent nBuONO, HCl Solvent diethyl ether Ref. 1 84368; Journal; JMCMAR; J.Med.Chem.; EN; 21; 1978; 623-628; Reaction Reaction ID 281755 Reactant BRN 1908501 2--1-phenyl-propanone-(1) Product BRN 507867 1-methyl-2-phenyl-ethylamine ------------------------- Reaction Details Reaction Classification Preparation Reagent palladium acetic acid sulfuric acid Other conditions Hydrogenation Ref. 1 1934222; Journal; JLACBF; Justus Liebigs Ann. Chem.; 560; 1948; 215,219; ------------------------------------------------------------------------------- Rhodium: Also see J. Med. Chem. 1991, 34(5), 1663 -------------------------------------------------------------------------------