N-phenyl amidines

Details N-phenyl amidines N-phenyl amidines

1975-10-24

1978-02-07

Rollins, Alton D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

544 59, 544164, 544143, 544144, 260296R, 26032615, 2603265D, 2603265L, 2603269, 260329AM, 2603323R, 2603325, 2603477, 260564RF, 424244, 424263, 424274, 544 60, 544 61, 544146, 544152, C07D20722, C07D21172, C07D22312, C07D40512

Patent

active

040726754

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 iminopyrrolidinylindoles 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-pyrrolidinyl]methyl]indole.

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