N-phenyl amidines

Details N-phenyl amidines N-phenyl amidines

1975-09-02

1977-09-20

Schwartz, Gerald A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

42424856, 2603437, 26050112, 26050114, 42424851, 424280, 424316, C07C12300

Patent

active

040497143

ABSTRACT:
N-Phenyl amidines which have diuretic, antithrombogenic, smooth muscle relaxant, anti-inflammatory and antiarrhythmic properties have been discovered. They are prepared by reacting a substituted aniline with a carboxamide selected from the group consisting of amides and lactams in the presence of phosphorus oxychloride. Typical examples of substituted N-phenyl amidines thus obtained are 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline, 2-(N-phenylbenzylamino)-1-pyrroline, 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole and 4,5,6,7,8,9-hexahydro-2-(N-phenylphenethylamino)-3H-azonine. Indole substituted N-phenyl amidines can be rearranged to provide iminopyrrolinidinylindoles which are useful as diuretic, antithrombogenic and smooth muscle relaxant agents. In the case of 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole, the rearranged product is 3-[[2-(p-methoxyphenylimino)-1-pyrrolindinyl]methyl]indole.

REFERENCES:
chemical Abstracts, vol. 31, 5774(a), (1937).
Chemical Abstracts, vol. 49, 10,227(a).
Chemical Abstracts, vol. 57, 14,975(b), (1962).

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