Reaktion #2446088

Reaktionsgleichung

1-(cyclohexyl(methyl)amino)propan-2-yl 4-isopropylbenzoate

methyl iodide

→

N-[2-((4-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide

Lösungsmittel

DCE

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resultant reaction mixture
2. 2
   SonstigeThe solvent was evaporated
3. 3
   Sonstigethe crude product was purified by column chromatography
4. 4
   SonstigeThe product isolated
5. 5
   Sonstigewas re-crystallized from methanol/ether
6. 6
   Sonstige99.65% (200 nm), RT 3.09 min

Vorschrift

To a solution of 1-(cyclohexyl(methyl)amino)propan-2-yl 4-isopropylbenzoate (0.5 g, 1.57 mmol) in DCE (5 mL, methyl iodide (0.2 mL, 3.15 mmol) was added. The resultant reaction mixture was stirred at rt for 16 hours. The solvent was evaporated, and the crude product was purified by column chromatography. The product isolated was re-crystallized from methanol/ether. Yield: 134.9 mg (18.65%). 1H NMR (400 MHz, DMSO-d6) δ 7.94-7.92 (d, J=8 Hz, 2 H), 7.43-7.41 (d, J=8 Hz, 2 H), 5.54-5.50 (m, 1 H), 3.95-3.89 (m, 1 H), 3.61-3.58 (d, J=14 Hz, 1 H), 3.40-3.34 (m, 1 H), 3.03-2.95 (m, 7 H), 2.22-2.20 (d, J=11 Hz, 1 H), 2.10-2.07 (d, J=11 Hz, 1 H), 1.86-1.83 (m, 2 H), 1.57-1.43 (m, 3 H), 1.36-1.35 (d, J=6 Hz, 3 H), 1.16-1.11 (m, 9 H). LCMS: m/z=331.8 [M+], RT=3.08 min (Column: Y, Program: P1). UPLC: 99.65% (200 nm), RT 3.09 min (Mobile phase: A. ACN, B. 0.05% HCOOH in water, Column: Gemini® NX C18 (50*4.6 mm) 3μ.

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