[C:1]([O:9][CH:10]([CH3:21])[CH2:11][N:12]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:13][CH3:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O([CH2:30][CH3:31])S(C(F)(F)F)(=O)=O.[Cl-:32].FF>C(Cl)Cl.CO.O>[Cl-:32].[C:1]([O:9][CH:10]([CH3:21])[CH2:11][N+:12]([CH2:30][CH3:31])([CH2:13][CH3:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1To 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)
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