Réaction #2446088

Équation de réaction

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

methyl iodide

→

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

Solvants

DCE

Conditions de réaction

Traitement

1. 1
   AutreThe resultant reaction mixture
2. 2
   AutreThe solvent was evaporated
3. 3
   Autrethe crude product was purified by column chromatography
4. 4
   AutreThe product isolated
5. 5
   Autrewas re-crystallized from methanol/ether
6. 6
   Autre99.65% (200 nm), RT 3.09 min

Mode opératoire

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.

Source