Sodium Iodide → HCID 67196008, compound

Participants

Reaction Conditions

Reaction Steps

4-(3-Methyl-4,5,5a,6,7,8,9,9a-octahydrobenzo[g]indazol-1-yl)phenol (1.49 mmol) was dissolved in N,N′-dimethylformamide (6 mL), and 1-(3-chloropropyl)pyrrolidine (0.22 g, 1.49 mmol), sodium hydride (72 mg, 60% dispersion in mineral oil, 1.79 mmol) and a catalytic amount of sodium iodide were added. The reaction was heated at 70° C. for 3 hours. The solution was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were dried over MgSO4 and concentrated. SiO2 chromatography with 2% triethylamine/10% methanol/ethyl acetate gave 0.268 g of the desired product. LC-MS (C25H35N3O calc'd 393) m/z 394 (M+H). 1H NMR (300 MHz, CDCl3) 7.27 (d, J=8.7 Hz, 2H), 6.91 (d, J=9 Hz, 2H), 4.05 (t, J=6.3 Hz, 2H), 2.64 (t, J=7.2 Hz, 2H), 2.58-2.39 (m, 7H), 2.20 (s, 3H), 2.07-2.00 (m, 2H), 1.82-1.10 (m, 14H), 0.91-0.79 (m, 1H).

Provenance & Evidence