Benzamide, 4-iodo-N-(1-methyl-4-piperidinyl)- synthesis

Yield:893420-30-9 88%

Reaction Conditions:

with triethylamine in tetrahydrofuran at 20; for 16.0833 h;

Steps:

29

4-Iodo-iY-( 1 -methylpiperidin-4-vObenzamide l-Methylpiperidin-4-amine (5.0 g, 43.8 mmol) and triethylamine (7.3 ml, 52.5 mmol) were stirred in THF (200 ml) under an inert atmosphere. 4-Iodobenzoyl chloride (11.7 g, 43.8 mmol) was added in portions over 5 mins. Stirring was continued for a further 16 hours, then the solvent was evaporated in vacuo and the residue partitioned between EtOAc (200 ml) and IM NaOH (100 ml). The organics were washed with water (100 ml) and brine (100 ml), dried and evaporated to afford the title compound as a colourless solid (13.2 g, 88%). NMR 8.26 (d, EPO IH), 7.82 (d, 2H), 7.61 (d, 2H), 3.77-6.62 (m, IH), 2.74 (d, 2H), 2.14 (s, 3H), 1.92 (t, 2H), 1.97-1.85 (m, 2H), 1.55 (ap. q, 2H); m/z 345.

References:

WO2006/64251,2006,A1 Location in patent:Page/Page column 69-70