Synthesis of iodomethylcholine iodide (IMC)

Synthesis procedure for iodomethylcholine iodide (IMC):
 

In a 250 mL round bottom flask, diiodomethane (4.8 mL, 60 mmol) was added to a stirred solution of dimethylethanolamine (5.0 mL, 50 mmol) in acetonitrile (50 mL) at room temperature. The flask was lightly capped with a rubber septum and the resulting solution stirred at room temperature for 48 h. The solvent was then removed by rotary evaporation and the resulting residue crystallized from absolute ethanol and suction filtered through grade 2 filter paper to give a light yellow solid that was dried under high vacuum overnight, 8.57 g, 48% yield.

¹H-NMR (400 MHz, D₂O): d 5.24 (s, 2H, ‑N-CH₂-I), 4.06-3.99 (m, 2H, ‑CH₂-CH₂-OH), 3.68-3.62 (m, 2H, ‑N-CH₂-CH₂-), 3.29 (s, 6H, ‑N(CH₃)₂);

¹³C-NMR (100 MHz, D₂O): d 66.1 (‑CH₂-CH₂-OH), 55.8 (‑N-CH₂-CH₂‑), 52.9 (‑N(CH₃)₂), 33.0 (‑N-CH₂-I);

HRMS (ESI/TOF): m/z (M⁺) calculated for C₅H₁₃INO, 230.0036; found, 230.0033.