2-[[(2,6-Di(Methyl-d3)phenyl)aMino]carbonyl]-1,1-diMethyl-piperidiniuM Iodide synthesis

Yield:345261-08-7 80%

Reaction Conditions:

in dichloromethane;water;

Steps:

2 (N-Methyl-Mepivacaine Iodide)

EXAMPLE 2 Synthesis of 2-{[(2,6-Dimethylphenyl)amino]carbonyl}-1,1-dimethylpiperidinium iodide (N-Methyl-Mepivacaine Iodide) Mepivacaine hydrochloride (2.92 g, 10.32 mmol) was dissolved in H₂O (15 mL), saturated aqueous NaHCO₃ (30 mL), and extracted with dichloromethane (3*50 mL). The organic layers were combined, dried over anhydrous Na₂SO₄, and concentrated in vacuo (50 mL). Methyl iodide (1.3 mL, 20.64 mmol) was then added to the filtrate and the reaction mixture was stirred at room temperature for 48 hours. The solvent was evaporated, and the resultant solid dissolved in water (200 mL). The aqueous solution was extracted with ether (2*200 mL) and then with CH₂Cl₂ (2*200 mL). The combined CH₂Cl₂ layers were dried over anhydrous Na₂SO₄, and the solvent was evaporated to give the product (3.19 g, 80% yield) as yellow crystals. ¹³C NMR (75 MHz, CDCl₃) δ18.9 (CH₃), 19.6 (CH₂), 20.2 (CH₂), 24.5 (CH₂), 46.4 (CH₃), 53.6 (CH₃), 65.0 (CH₂), 69.9 (CH), 127.8 (CH), 128.2 (CH), 132.4 (C), 134.9 (C), 164.7 (C).]

References:

US2003/166629,2003,A1