Réaction #2446082

Équation de réaction

1-(cyclohexyl(methyl)amino)propan-2-yl 2,4,6-trimethylbenzoate

methyl iodide

→

N,N-dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide

Solvants

DCM

DCE

Conditions de réaction

Traitement

1. 1
   AutreThe resultant reaction mixture
2. 2
   Concentrationconcentrated to dryness

Mode opératoire

To a solution of 1-(cyclohexyl(methyl)amino)propan-2-yl 2,4,6-trimethylbenzoate (0.30 g, 0.946 mmol) in DCE (5 mL), methyl iodide (0.12 mL, 1.892 mmol) was added. The resultant reaction mixture was stirred at rt for 16 hours. The reaction mixture was diluted with DCM and concentrated to dryness. The crude product was subjected to column chromatography to obtain N,N-dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide. Yield: 0.109 g (25%). 1H NMR (400 MHz, CDCl3) δ 6.86 (s, 2 H), 5.70-5.67 (m, 1 H), 4.52-4.48 (d, J=14 Hz, 1 H), 3.83-3.77 (m, 1 H), 3.70-3.64 (m, 1 H), 3.34 (s, 3 H), 3.28 (s, 3 H), 2.29-2.01 (m, 10 H), 2.01-1.98 (m, 1 H), 1.84 (m, 1 H), 1.64-1.62 (d, J=6 Hz, 4 H), 1.47-1.38 (m, 4 H), 1.13-1.08 (m, 2 H). LCMS: m/z=332.2 [M+], RT=3.01 min (Column: Y, Program: P1). HPLC: 99.53% (200 nm), RT 4.11 min (Mobile phase: A: ACN, B: 0.05% TFA in water, Column: Zorbax® SBC18 (50*4.6 mm) 1.8μ.

Source