反応 #2446087

反応方程式

chloride

chloride

1-(cyclohexyl(ethyl)amino)propan-2-yl benzoate

ethyl triflate

fluorine

→

N-[2-(benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride

溶媒

water

methanol

DCM

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% methanol/DCM
4. 4
   その他to provide a sticky liquid
5. 5
   workup.STIRRINGstirred for 6 hours
6. 6
   ろ過The solution was then filtered
7. 7
   濃縮concentrated
8. 8
   その他to provide a solid
9. 9
   ろ過filtered
10. 10
    濃縮The filtrate was concentrated

実験手順

To a stirred solution of 1-(cyclohexyl(ethyl)amino)propan-2-yl benzoate (0.427 g, 1.47 mmol) in dry DCM (20 mL) was added ethyl triflate (0.25 mL, 1.92 mmol) dropwise at ice-cold conditions. The resulting 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% methanol/DCM to provide a sticky liquid. Amberlite® IRA-400 (Cl) chloride form resin (3.0 g) was added to a solution of the liquid compound in methanol (15 mL) and stirred for 6 hours. The solution was then filtered, concentrated and lyophilized to provide a solid. Because the fluorine NMR spectrum showed incomplete counter ion exchange, the solid was again treated with Amberlite® IRA-400 (Cl) chloride form resin in water and filtered. The filtrate was concentrated and the crude material was lyophilized to provide N-[2-(benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride as an off white solid. Yield: 0.05 g (9.62%). 1H NMR (DMSO-d6) δ 7.98 (d, J=8 Hz, 2 H), 7.68 (t, J=7 Hz, 1 H), 7.54 (t, J=8 Hz, 2 H), 5.52-5.49 (m, 1 H), 3.95-3.89 (m, 1 H), 3.55 (d, J=15 Hz, 1 H), 3.44-3.35 (m, 5 H), 2.19-2.17 (m, 1 H), 2.09-2.06 (m, 1 H), 1.80-1.78 (m, 2 H), 1.54-1.51 (m, 3 H), 1.36 (d, J=6 Hz, 3 H), 1.25-1.07 (m, 9 H). LCMS: m/z=318.0 [M+], RT=2.88 min, (Column: Y, Program: P1). UPLC: 98.70% (200 nm), RT=3.59 min, (Mobile Phase A. 0.05% TFA in water, B. Acetonitrile; Column: Zorbax® SB-C18 (4.6×50 mm) 1.8μ)

出典