Triethylamine → HCID 86758494, compound

Participants

Reaction Steps

To a stirring solution of 2-[1-benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-pyrimidine-5-carboxylic acid (375 mg, 0.93 mmol) in 10 mL of CH2Cl2 at room temperature was added oxalyl chloride (0.11 mL, 0.12 mmol) and 0.01 mL DMF. After 1 hour, triethyl amine (0.52 mL, 3.72 mmol) and 2-amino-2-methyl-propan-1-ol (0.13 mL, 1.39 mmol) was added and the resulting mixture stirred for 60 minutes. The reaction was quenched by the addition of NaOH and poured into CH2Cl2. The layers were separated, the aqueous layer was extracted with CH2Cl2 (3×20 mL), and the combined organic layers were dried, filtered and concentrated to yield 350 mg of the desired product. 1HNMR (400 MHz, CDCl3) δ 8.98 (s, 2H), 7.28-7.21 (comp, 5H), 7.15 (t, 1H), 6.94-6.91 (comp, 2H), 6.65 (d, 1H), 6.29 (br s, 1H), 3.73 (s, 3H), 3.65 (s, 2H), 3.38 (s, 2H), 2.98-2.96 (comp, 2H), 2.85-2.76 (comp, 2H), 2.33-2.21 (comp, 2H), 2.11-2.08 (comp, 2H), 1.39 (s, 6H); MS (M+1) 475.1.

Provenance & Evidence