反応 #2446082

反応方程式

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

溶媒

DCM

DCE

反応条件

後処理

1. 1
   その他The resultant reaction mixture
2. 2
   濃縮concentrated to dryness

実験手順

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.

出典