In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 115279-73-7 as follows. Safety of 1-(4-Aminophenyl)cyclopentanecarbonitrile
To a jacketed reactor were charged 71 (1.0 equiv), 10% Pd/C (7.0 wt %), and MeOH (10 vols). The contents of the reactor were inerted with N2 and then pressurized with H2 to 6.0 bar. The jacket was initially set to 18 C. to contain the minor exotherm that ensued. After 2 h, the jacket temperature was adjusted to 35 C. to achieve an acceptable reaction rate. The reaction mixture was stirred under these conditions overnight. HPLC analysis of an aliquot of the reaction mixture revealed that conversion to the intermediate aniline was complete (<0.1% of the hydroxylamine intermediate remaining) To the reactor were then charged AcOH (1.0 equiv), formaldehyde (37% solution in MeOH, 2.7 equiv), and 10% Pd/C (3.0 wt %). The reaction mixture was again inerted with N2 and then pressurized with H2 to 6.0 bar and heated to 45 C. (0160) After 2 h, HPLC analysis indicated that the reaction was complete (<0.1% monomethyl intermediate remaining) The reaction mixture was inerted with N2 and then filtered through Celite while still at 45 C. The reactor and cake were washed with additional MeOH (2.0 vols), and the resulting filtrate was transferred to a clean jacketed reactor vessel. The solution was then distilled down to a level of 10 vols while maintaining a pot temperature of 40-50 C. (jacket temperature 55 C., 250 torr). This led to a homogenous solution at the conclusion of the distillation. The solution was then cooled to 20 C. over 1 h. Crystallization began to occur at 33 C. Water (5.0 vols) was then added dropwise over 1 h while maintaining the batch temperature at 20 C. The resulting slurry was aged overnight and then filtered. The reactor and filter cake were washed with ice-cold 1:1 MeOH:H2O (5.0 vols). After drying under vacuum at 40-45 C. to constant weight, 72 was obtained in 90% yield with an HPLC purity of 96.0% (2.8% dimer-related impurity).
According to the analysis of related databases, 115279-73-7, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Atterocor, Inc.; Hunt, III, Stephen Warren; Phillips, Martin Douglas; Matunas, Robert; Chen, Herman; Betancourt, Aimesther; Uzarama, Charles; Thibert, Roch; (31 pag.)US2016/90354; (2016); A1;,
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