With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7149-42-0,(1-Methylpiperidin-4-yl)methanamine,as a common compound, the synthetic route is as follows.
7149-42-0, A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h – 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1-methyl-4-piperidinyl)methylamineHPLC-MS (method 1 ): Rt = 3.28 min, [M+H]+ m/z 492.1. NMR (300 MHz, DMSO-d6) delta 8.58 (s, 1 H), 8.43 (d, J = 7.9 Hz, 1 H), 8.20 (s, 1 H), 7.69 (m, 1 H), 7.49 (m, 1 H), 6.91 (s, 1H), 4.46 (m, 1 H), 3.20 (m, 4H), 2.80 (m, 2H), 2.70 (s, 3H), 2.17 (s, 3H), 1.89 (m, 3H), 1.72 (m, 2H), 1.46 (d, J = 6.2 Hz, 3H), 1.25 (m, 2H).
As the paragraph descriping shows that 7149-42-0 is playing an increasingly important role.
Reference£º
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); GARCIA COLLAZO, Ana Maria; PASTOR FERNANDEZ, Joaquin; BLANCO APARICIO, Carmen; RODRIGUEZ HERGUETA, Antonio; MARTIN HERNANDO, Jose Ignacio; RAMOS LIMA, Francisco Javier; HERNANDEZ HIGUERAS, Ana Isabel; SALUSTE, Carl-Gustave Pierre; GONZALEZ CANTALAPIEDRA, Esther; MARTINEZ GONZALEZ, Sonia; SALGADO SERRANO, Antonio; NOYA MARINO, Beatriz; WO2011/80510; (2011); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem