-------------------------------------------------------------------------------
                      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

-------------------------------------------------------------------------------




