Extracurricular laboratory: Synthetic route of 226942-29-6

226942-29-6, As the rapid development of chemical substances, we look forward to future research findings about 226942-29-6

6-Bromo-1,2,3,4-tetrahydroisoquinoline, cas is 226942-29-6, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

Step A: Preparation of l-(6-Bromo-3,4-dihydroisoquinolin-2(lH)-yl)-2- hydroxyethanone. A magnetically stirred flask equipped with a drying tube was charged with a solution of6-bromo-l,2,3,4-tetrahydroisoquinoline (3.43 g, 16.2 mmol) in anhydrous toluene (40 mL), to which was added 2,2-dimethyl-l,3-dioxolan-4-one (1.9 g, 16.2 mmol). The resulting solution was refluxed for 20 h. The reaction mixture was cooled, extracted with 1 N HCl (30 mL), followed by brine (20 mL), and the organic extract was dried over MgSO4. The resulting solution was reduced in volume to about 25 mL, and heptane (25 mL) was gradually added over 20 min as precipitate formed. The resulting white solid was collected by filtration and rinsed with 1 : 1 toluene/heptane to provide the title compound. LCMS m/z = 270.1 [M+H]+; 1H NMR (400 MHz, CDCl3) delta 2.48 (bs, IH), 2.87-2.94 (m, 2H), 3.55 (t, J= 5.9 Hz, 1.2H), 3.89 (t, J= 6.1 Hz, 0.8H), 4.26 (s, 2H), 4.40 (s, 0.8H), 4.75 (s, 1.2H), 7.00 (d, J= 8.3 Hz, 0.4H), 7.07 (d, J= 8.3 Hz, 0.6H), 7.32-7.39 (m, 2H).

226942-29-6, As the rapid development of chemical substances, we look forward to future research findings about 226942-29-6

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/105206; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem