C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/247.8
C07D 265/30 (2006.01)
Patent
CA 1070689
ABSTRACT OF THE DISCLOSURE: Novel 2-(2-hydroxyethyl) tetrahydro-1,4-oxazines of the general formula: Image (I) wherein Ar and Ar1 are the same or different and represent an unsubstituted or halogen-substituted phenyl and R is a lower alkyl having from 1 to 4 carbon atoms, and the quaternary salts thereof having the formula: Image (II) wherein Ar, Ar1 and R are as defined above, R1 is a lower alkyl having from 1 to 4 carbon atoms and X is C1, Br, I or CH3SO4, are prepared by reacting a 2-cyanomethyl tetrahydro-1,4-oxazine of the formula: Image (III) wherein R is as defined above, with HC1 in an EtOH medium, hydrolysing the product obtained and then treating it with anhy- drous NH3 to obtain the corresponding ester and reacting the ester thus obtained with at least one organomagnesium compound of the formula Ar-MgX' or Ar1-MgX' in which Ar and Ar1 are as defined above and X' is a halogen atom to produce the desired 2-(2-hydroxyethyl) tetrahydro-1,4-oxazine of the formula (I); when a quaternary salt of the formula (II) is desired, the tertiary amine thus obtained is reacted with a compound of the formula R1X in which R1 and X are as defined above to provide the corresponding quaternary derivative. The compounds of the invention are useful for treating spasmodic syndromes.
261986
Busch Norbert
Mauvernay Roland-Yves
Moleyre Jacques
Monteil Andre
Simond Jacques
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