Hydrochloric Acid → HCID 59293914, compound

Participants

Reaction Steps

4-(3-Methylsulfanyl-phenyl)-1-propyl-1,2,3,6-tetrahydropyridine (2) (290 mg, 1.17 mmol) was brought in a Parr-flask with 10 mL of ethanol (100%) in a nitrogen atmosphere. 100 mg of Pd/C and 0.5 mL of HCl (37%) were added. The flask was attached to a Parr reduction apparatus and H2 gas was added to a pressure of 3 Bar. It was left shaking for 1 h. Then, the mixture was filtered over celite, put back in the flask and another 100 mg of Pd/C and 1 ml of HCl (37%) was added before attaching the flask to the Parr apparatus again and starting another session of 75 min this time. This procedure was repeated another 3 times, with session durations of 105 min, 1 night and 2 h. Eventually, the mixture was filtered, the solvent evaporated in vacuo on a rotavapor. 10 mL of NaHCO3 10% was added (pH 8). Then 30 mL of water and 40 mL of diethyl ether were added and shaken. The aqueous layer was extracted three times with diethyl ether. The combined organic layers were washed with brine, dried on MgSO4, filtered and the solvent was evaporated on a rotavapor. The slightly yellow oil was taken up in CH2Cl2 and purified by gradient column chromatography (Al2O3, CH2Cl2, CH2Cl2:MeOH 10:1). Fractions 9-20 contained the desired product. The fractions were collected and the solvent was evaporated in under reduced pressure. Yield: 335 mg (115%). The reaction was followed on thin layer chromatography (SiO2 flushed with NH3, CH2Cl2:MeOH 20:1 and Al2O3, CH2CL2:MeOH 40:1). 1H-NMR (CDCl3, 300 MHz): δ 7.2 (m), 3.1 (t), 2.5 (s), 2.4 (m), 2.0 (m), 1.8 (m), 1.6 (m), 1.2 (m), 0.9 (m) ppm; 13C-NMR (CDCl3, 300 MHz): δ 145.673, 136.767, 127.345, 126.882, 126.722, 125.372, 124.576, 123.650, 123.430, 122.793, 122.216, 120.479, 59.631, 52.841, 41.333, 31.888, 26.630, 18.680, 14.287, 10.577 ppm; GCMS (EI): m/z 249 (M+), 220 (M−29); GC (100-320° C., 10° C./min): 4.7, 9.9 min.

Provenance & Evidence