Potassium Carbonate → 3-Aminopropyl-4-methyl-4-phenylpiperidine

Participants

Reaction Steps

A solution of 4-methyl-4-phenylpiperidine (1.00 g, 5.70 mmol), 3-bromopropylamine hydrobromide (1.87 g, 8.55 mmol) and potassium carbonate (1.97 g, 14.2 mmol) in refluxing dioxane (20 mL) was stirred for 36 hours. After removal of the solvent, water (50 mL) was added and the pH adjusted to 11-12 by the addition of 1 N aqueous NaOH. The mixture was extracted with CH2Cl2 (150 mL+3×100 mL) The combined organic solutions were dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography (CHCl3/MeOH/2 N NH3 in MeOH 100/20/10), giving the desired product as a colorless oil (241 mg, 18%): 1H NMR δ 1.18 (s, 3 H), 1.61 (p, J=7 Hz, 2 H), 1.75 (m, 2 H), 2.10 (m, 2 H), 2.33 (t, J=7 Hz, 2 H), 2.40 (m, 2 H), 2.45 (m, 2 H), 2.72 (t, J=6 Hz, 2 H), 3.02 (br s, 2 H), 7.14 (m, 1 H), 7.30 (m, 4 H); 13C NMR δ 30.28, 36.78, 37.64, 41.51, 50.96, 57.51, 126.16, 126.40, 128.91, 149.20.

Provenance & Evidence