Reference of 20781-20-8,Some common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Step 1: N-(2-((tert-Butyldimethylsilyloxy)methyl)- l-methyl-6,7,8,9-tetrahydrocyclohepta[f]indol-5( lH)-ylidene)- 1 -(2,4-dimethoxyphenyl)methanamine To solution of 2-((tert-butyldimethylsilyloxy)methyl)-l-methyl-6,7,8,9-tetrahydrocyclohepta[f]indol-5(lH)-one (Intermediate 4, 7.458 g, 20.86 mmol) in CH2C12(65 mL) was added 2,4-dimethoxybenzylamine (3.30 mL, 21.97 mmol) and NEt3(7.80 mL, 55.96 mmol). The mixture was cooled to 0 C before TiCl4solution (1M CH2C12, 13.60 mL, 13.60 mmol) was added dropwise via syringe pump over 30 min. The reaction was allowed to warm to room temperature and stirred overnight. The mixture was diluted with CH2C12(150 mL) and then quenched with NaHC03(aq. satd., 50 mL). Upon vigorous shaking, the organic phase was separated with a PTFE phase separator and then dried over Na2S04. Removal of the solvent afforded the product (10.6 g, quant.) as yellow oil which was taken directly into next step without purification.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2,4-Dimethoxyphenyl)methanamine, its application will become more common.
Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem