US 4,539,413 AGranted

Preparation of 3-amino-1-[(1,4-benzodioxan)-2-yl-methoxy]-2-propanols

AssigneePierre Fabre S.A.

InventorsGilbert Mouzin, Henri Cousse, Pol Vilain

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Abstract

The present invention concerns a novel process for the production of new chemical compounds of the general formula: ##STR1## in which: R.sub.1 and R.sub.2 may be identical or different and represent a hydrogen or halogen atom or else a lower alkyl, lower alkoxy, nitro or acetyl group and R represents a lower alkyl or lower aralkyl group, such as benzyl. These compounds are useful in therapy for the treatment of hypertension and cardiac arrhythmia. The novel process involves reaction of a 2-hydroxymethyl-1,4-benzodioxan with epichlorohydrin to produce an intermediate glycidyl ether, which is then reacted with a primary amine to produce the final 3-amino-1-[(1,4-benzodioxan)-2-yl-methoxy]-2-propanol or an acid addition salt thereof.

Claims11

Dependent claims

A method of preparing a compound of the formula ##STR18## in which R.sub.1 and R.sub.2 may be identical or different and represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, nitro or acetyl group, and

R represents a lower alkyl or lower aralkyl group, or a salt thereof with a therapeutically-acceptable inorganic or organic acid, characterized by the step of reacting a glycidyl ether of formula III ##STR19## with a primary amine of formula IV
R--NH.sub.2
in a solvent for the reaction, for a period of time and at a temperature sufficient to produce the desired compound of formula I, and also characterized by the additional step of first producing the glycidyl ether of formula III by reaction of a 2-hydroxymethyl-1,4-benzodioxan of formula II ##STR20## in which R.sub.1 and R.sub.2 have the same meanings as those given in the foregoing, with epichlorohydrin in the presence of a base and in the presence of a catalyst of the quarternary ammonium type.

Dependencies are inferred from the claim text.