Hydrochloric Acid → HCID 69215403, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[4-(3-piperidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-carbonitrile (1.45 g, 4.4 mmol), isopropanol (12 mL), concentrated HCl (350 μL), and PtO2 (115 mg) was stirred and hydrogenated to 50° C. overnight at atmospheric pressure. The mixture was filtrated over diatomaceous earth and concentrated. The residue was dissolved in DCM/MeOH mixture and washed with NaOH (1M). The organic layers were dried over Na2SO4, filtered and concentrated, purified by flash chromatography (10 g silica gel, DCM/MeOH (10% NH3)) to provide the title compound as free base (0.650 g, 44.5%). This was then converted to the dihydrochloride salt. 1H NMR (400 MHz, DMSO-D6) δ 10.66 (bs, 1H), 7.74 (bs, 3H), 7.32 (d, 2H), 6.97 (d, 2H), 4.07 (t, 2H), 3.73-3.65 (m, 2H), 3.47-3.28 (m, 4H), 3.18-3.10 (m, 2H), 2.98-2.81 (m, 4H), 2.25-2.16 (m, 2H), 2.14-2.06 (m, 2H), 1.90-1.67 (m, 7H), 1.44-1.31 (m, 1H).

Provenance & Evidence