7-Bromo-1,2,3,4-tetrahydroisoquinoline

To a solution of methanol (50 mL) and saturated sodium carbonate solution (50 mL) is added l-(7-Bromo-3, 4-dihydro-lH-isoquinolin-2-yl)-2, 2, 2-trifluoro-ethanone (14.3 g, 46.4 mmol). The reaction mixture is stirred at 60 C for 1 h, concentrated and the residue is extracted with ethyl acetate. The combined organic layers are washed with water and brine, dried (NaTo a mixture of the product from Step A (26 g, 88 mmol) and paraformaldehyde (5.6 g, 130 mmol), was added in one portion a mixture of concentrated sulfuric acid (130 mL) and glacial acetic acid (195 mL), and the resulting mixture stirred at room temperature for 17 hours. The reaction mixture was poured onto ice/water (1.5 L) and extracted with ethyl acetate (3 x 300 mL), the combined ethyl acetate layers were washed with water (2 x 600 mL), sat NAHC03 (300 mL), and saturated NaCl (150 ML), dried over MGS04, filtered and evaporated in vacuo. The residue was dissolved in ethanol (450 mL), and a solution of potassium carbonate (60 g, 434 mmol) in water (150ML) was added. The mixture was heated to reflux for 1 hour then cooled and evaporated in vacuo. Water (500 mL) was added to the residue and extracted with CH2CI2 (3 x 300 mL); the combined CH2CI2 layers were washed with water (500 mL), sat NACI (150 mL), dried over NA2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica elution with 5percent CH30H in CH2CI2 containing 0. 5percent NH40H to give the product (10 g, 54percent) ; H NMR 500MHZ (CDCL3) 8 = 1.77 (1H, br s), 2.77 (2H, d, J = 6.0 Hz), 3.11 (2H, t, J = 6.0 Hz), 3.97 (2H, s), 6.95 (1H, d, J = 8.0 Hz), 7.15 (1H, s) 7.23 (1H, dd, J = 1. 2 and 8. 2 Hz).7-Bromo-2-(4-(4-phenylbenzoylamino)butyl)-1, 2, 3, 4-tetrahydroisoquinoline 7-Bromo-2-tufluoroacetyl-1, 2, 3, 4-tetrahydroisoquinoline (7.20 g, 23 mmol) and potassium carbonate (16.8 g, 122 mmol) in 10% aqueous methanol (250 ml) were heated at reflux, with stirring, for 2 h. After cooling the solvents were removed in vacuo and the residue was partitioned between water (200 ml) and dichloromethanc (100 ml). The aqueous layer was extracted further with dichloromethane (2*50 ml). The combined organics were washed with brine, dried Na2 SO4) and evaporated in vacuo to afford 7-bromo1, 2, 3, 4-tetrahydroisoquinoline as a brown oil (4.50 g, 21 mmol, 92%).

Molecular Weight:212.09
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:210.99966
Monoisotopic Mass:210.99966
Topological Polar Surface Area:12
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes