反応 #2446085

反応方程式

1-(cyclohexyl(methyl)amino)propan-2-yl 2-isopropylbenzoate

methyl iodide

→

N-[2-((2-isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide

溶媒

DCE

反応条件

後処理

1. 1
   濃縮The reaction mixture was concentrated
2. 2
   その他the crude material was purified by Combiflash® chromatography
3. 3
   洗浄eluting with 3-4% CH3OH/DCM
4. 4
   その他to provide a solid which
5. 5
   その他was crystallized from methanol-ether

実験手順

To a stirred solution of 1-(cyclohexyl(methyl)amino)propan-2-yl 2-isopropylbenzoate (0.45 g, 1.41 mmol) in DCE (3 mL) was added methyl iodide (0.35 mL, 5.67 mmol) and the reaction mixture was stirred at rt for 16 hours in a sealed tube. The reaction mixture was concentrated and the crude material was purified by Combiflash® chromatography, eluting with 3-4% CH3OH/DCM to provide a solid which was crystallized from methanol-ether to provide white N-[2-((2-isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide. Yield: 0.415 g (64%). 1H NMR (DMSO-d6) δ 7.71 (d, J=8 Hz, 1 H), 7.58-7.50 (m, 2 H), 7.31 (t, J=7 Hz, 1 H), 5.57-5.54 (m, 1 H), 3.93-3.87 (m, 1 H), 3.67-3.57 (m, 2 H), 3.38-3.34 (m, 1 H), 3.05 (s, 3 H), 3.02 (s, 3 H), 2.17-2.08 (m, 2 H), 1.87-1.84 (m, 1 H), 1.75-1.72 (m, 1 H), 1.54-1.42 (m, 3 H), 1.40 (d, J=6 Hz, 3 H), 1.24-1.19 (m, 7 H), 1.13-0.99 (m, 2 H). LCMS: m/z=332.0 [M+], RT=3.01 min, (Column: Y, Program: P1). UPLC: 98.43% (200 nm), RT=3.60 min (Mobile Phase A. 0.05% TFA in water, B. Acetonitrile; Column: Zorbax® SB-C18 (4.6×50 mm) 1.8μ)

出典