GB1399015A — Fluoroalkylated phenylethylamine derivatives

USPTO Abstract

1399015 N - (fluoroalkyl) - phenethylamines DEUTSCHE GOLD - UND SILBERSCHEIDEANSTALT 25 Aug 1972 [28 Aug 1971] 39698/72 Heading C2C Novel compounds I in which (F) n -Alk is a straight or branched fluoroalkyl radical having 2 to 6 C atoms and a fluorine atom, R<SP>1</SP> is hydrogen or methyl, R<SP>2</SP> is hydrogen or hydroxyl, each R<SP>3</SP> which may be the same or different is hydrogen, hydroxy, C 1-6 alkyl or C 1-6 alkoxy, and m is 1 or 2 and their acid-addition salts are prepared by (1) reaction with or without solvent or suspension agent of (F) n -Alk-Z with a compound III in which R<SP>2</SP> is oxygen or R<SP>2</SP> and hydrogen and one of X and Z is amino and the other chlorine, bromine or alkyl- or aryl-sulphonyloxy or X with one bond of R<SP>2</SP> is oxygen the other bond of R<SP>2</SP> being hydrogen and if R<SP>2</SP> is oxygen this is subsequently reduced to hydroxy or (2) reaction of (F) n -Alk<SP>1</SP>-V with a compound V in which (F) n -Alk<SP>1</SP> is a fluoroalkyl group containing one C atom less than (F) n -Alk- V is -CH 2 -NH 2 and W is the group CR<SP>1</SP>O or W is -CHR 1 -NH 2 and V is CHO, COOH-COCl, COBr or carboalkoxy the reaction being carried out with simultaneous or subsequent reduction. During these reactions any phenolic hydroxy or amino groups may be protected by groups which are subsequently split-off, (F) n -Alk is 2-fluoroethyl-, 3-fluoropropyl, 4-fluorobutyl, 5 - fluoropentyl-, or 6 - fluorohexyl. R 3 is preferably in the o- or p-position when m is 1 and in the 3,4- or 3,5-position when m is 2. Compounds I may be isolated as optical active isomers when they contain an asymmetric C atom. Compounds I have appetite-curbing properties, are mild stimulants and show broncholytic effects, and form with a carrier or diluent a pharmaceutical composition which may be adminstered orally or parenterally.