BUTTPARK 52\04-72 synthesis

Yield:851202-94-3 53%

Reaction Conditions:

Stage #1: 1-(6-bromo-1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-onewith copper(I) cyanide in DMF (N,N-dimethyl-formamide); for 18 h;Heating / reflux;
Stage #2: with ammonia in DMF (N,N-dimethyl-formamide);water;

Steps:

1-(6-Bromo-3, 4-dihydro-2H-quinolin-l-yl)-ethanone (96 mmol) was dissolved in DMF (60 mL) and CuCN (200 mmol) was added. The reaction mixture was refluxed for 18h, then cooled and poured into water (400 mL). Aq. NH3 (sat. ) (100 mL) was added, and the mixture was stirred vigorously until it had turned blue. The product had precipitated and was removed by filtration, washed with water and dried. Yield: 53% 1H NMR (D6-DMSO) : 1.78 (m, 2H); 2.67 (m, 2H); 3.23 (m, 2H); 6.43 (d, 1H); 7.41- 7.47 (2H). m/z: 201 (MH+)

References:

WO2005/39572,2005,A1 Location in patent:Page/Page column 31