On October 10, 2002, Mattson, Ronald; Denhart, Derek; Deskus, Jeffrey; Ditta, Jonathan; Marcin, Lawrence; Epperson, James; Catt, John; King, Dalton; Higgins, Mendi published a patent.Reference of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile The title of the patent was Preparation of cyclopropylindoles as selective serotonin reuptake inhibitors. And the patent contained the following:
Treatment of depression, anxiety disorders, premature ejaculation, chronic pain, obsessive-compulsive disorder, feeding disorders, premenstrual dysphoric disorder, panic disorders and psychotic disorders including bipolar disorder and schizophrenia. Title compounds [I; A1, A2 = alkylene, bond; A3 = alkylene, alkylidene; A4 = alkylene, bond; X, X1, X2 X3 = C, CH; J = alkyl; p = 0, 1; R1, R2 = H, alkyl, (substituted) cycloalkyl, Ph, PhO , NHCO2alkyl, alkylNHCO2, thienyl, furanyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, pyridyl, pyrimidinyl, piperidinyl, piperazinyl, morpholino, adamantyl, indolyl, isoindolyl, indolinyl, quinolinyl, dihydroquinolinyl, tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl; or A1R1 and A2R2 together with the N to which they are attached = pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, pyridyl, pyrimidinyl, piperidinyl, piperazinyl, morpholino, adamantyl, indolyl, isoindolyl, indolinyl, quinolinyl, dihydroquinolinyl, tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl and are optionally substituted with halo, alkyl, alkoxy, cyano, benzyl; R3 = H, alkyl; m = 0, 1; R4, R5 = H, cyano, halo, NO2, perfluoroalkyl; n = 0, 1; G = N, O, S; G1 = N, CH; Y = DH; D = C; Z = EH; E = C; with provisos], were prepared for treatment of depression, anxiety, premature ejaculation, chronic pain, obsessive-compulsive disorder, feeding disorders, premenstrual dysphoric disorder, panic disorder, and psychotic disorders including bipolar disorder and schizophrenia. Thus, a solution of di-Et (N-methoxy-N-methylcarbamoylmethyl)phosphonate in THF was added to a stirred suspension of sodium hydride in THF at 0°; the reaction was warmed to room temperature and was stirred for 2 h; After cooling to 0°, [5-cyano-1-(p-toluenesulfonyl)indol-3-yl]carboxaldehyde (preparation given) was added. The resulting mixture was stirred at 0° for 1 h to give 91% (E)-[5-cyano-1-(p-toluenesulfonyl)indol-3-yl]-N-methoxy-N-methylacrylamide. This was converted to trans-2-(5-cyanoindol-3-yl)-1-(N,N-dimethylaminomethyl)cyclopropane in several steps. The latter showed serotonin transporter binding with Ki<1 nM. The experimental process involved the reaction of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile(cas: 13544-06-4).Reference of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile
The Article related to cyclopropylindole preparation selective serotonin reuptake inhibitor, indole cyclopropyl preparation selective serotonin reuptake inhibitor, depression anxiety premature ejaculation obsessive compulsive disorder treatment cyclopropylindole, feeding disorder premenstrual dysphoric disorder panic disorder treatment cyclopropylindole and other aspects.Reference of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts