Triethylamine → HCID 19925648, compound

Participants

Reaction Steps

To a methylene chloride (16 mL) solution of 4-{3-[4-(N-methylamino)phenylthio]phenyl}-4-methoxytetrahydropyran (517 mg, 1.57 mmol; prepared in step 8 of Example 29) was added triethylamine (0.22 mL, 1.57 mmol) and triphosgene (23.3 mg, 0.79 mmol) in methylenechloride (5 mL). The resulting solution was stirred at ambient temperature for 0.5 h, N-methylpiperazine (0.70 mL, 6.3 mmol) was added, and the mixture was stirred for another hour at ambient temperature. The reaction mixture was partitioned between ethyl acetate and 10% aqueous HCl. The layers were separated and the organic layer was washed (1×, saturated sodium bicarbonate; 2×, water; 2×, brine), dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was chromatographed over silica gel (5% ethanol:methylene chloride+1% ammonium hydroxide) to give a light yellow oil. The oil was dissolved in ethyl acetate, treated with decolorizing carbon, and filtered through a celite pad. Removal of the volatiles under vacuum and drying the residue under high vacuum provided the title compound as a colorless oil (482 mg, 67%). 1H NMR (300 MHz, CDCl3) δ7.48 (1H, m), 7.15-7.38 (5H, m), 7.04 (2H, d, J=9 Hz), 3.77-3.89 (4H; m), 3.2-3.28 (4H; m), 3.24 (3H, s), 2.97 (3H, s), 2.20-2.28 (4H; m), 2.24 (3H; s), 1.88-2.04 (4H, m). MS m/e (M+H)+ =456; Analysis calc'd for C25H33N3O3S: C, 65.91; H, 7.30; N, 9.22. Found: C, 65.86; H, 7.25; N, 9.22.

Provenance & Evidence