Process for preparing .alpha.-[(alkylamino)methyl]-.beta.-arylox

Details Process for preparing .alpha.-[(alkylamino)methyl]-.beta.-arylox Process for preparing .alpha.-[(alkylamino)methyl]-.beta.-arylox

1981-08-10

1983-08-30

Hines, Robert V.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

26050118, 424316, 424330, 564142, 564161, 564170, 564172, 564175, 564349, 549525, 549548, C07C 8300

Patent

active

044018320

ABSTRACT:
Disclosed herein are .alpha.-[(alkylamino)methyl]-.beta.-aryloxy-benzeneethanols exhibiting antiarrhythmic activity and having the following formula: ##STR1## wherein R is hydrogen, halogen, lower alkyl, or lower alkoxy; X is phenyl, 1-naphthyl, or a phenyl group substituted by a halogen, a lower alkyl group, or a lower alkoxy group; R.sub.1 is lower alkyl; and pharmacologically acceptable acid addition salts thereof. Also disclosed is a process for the addition of an aryloxy group at the 3-position of a 3-phenyl-2-oxiranecarboxamide to produce an .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamide, said process comprising contacting an alkali metal aryloxide with said 3-phenyl-2-oxiranecarboxamide in the presence of a crown ether. Such .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamides may then be reduced to produce the compounds of the invention.

REFERENCES:
patent: 2336093 (1944-12-01), Grun et al.
patent: 2695919 (1954-11-01), Wright et al.
patent: 2920079 (1960-01-01), Hudson
patent: 3106564 (1963-10-01), Fleming et al.
Pedersen, C. J., "Cyclic Polyethers and their Complexes with Metal Salts", J. Am. Chem. Soc., 89, 7017-7036 (1967).
Knipe, A. C., "Crown Ethers", J. Chem. Ed., 53, 618-622 (1976).
Fieser, M. & Fieser, L. F., Reagent for Organic Synthesis, vol. 5, pp. 152-155 (John Wiley & Son, N.Y. 1975).
Thomassen, L. M., "The Effect of the Solvent on the Reactivity of Potassium Phenoxide in Nucleophilic Substitution Reactions, Part IV, Cyclic Polyethers as Additives", Acta. Chem. Scand., 25, 3024-3030 (1971).

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