Methyl iodide → Docosahexaenoyl choline iodide

HRID 1859091Notes

Reaction equation

HRID 1859091 reaction equation
[C:1]([O:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])(=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[I:30][CH3:31]>C(Cl)Cl>[I-:30].[C:1]([O:24][CH2:25][CH2:26][N+:27]([CH3:31])([CH3:29])[CH3:28])(=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 543902942-Dimethylaminoethyl docosahexaenoate

Product 1

HCID 86754749Docosahexaenoyl choline iodideYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-dimethylaminoethyl docosahexaenoate (1.12 g, 2.80 mmol) in CH2Cl2 (10.0 mL) was added iodomethane (0.80 g, 5.60 mmol) dropwise at room temperature. The mixture was stirred at room temperature for 3 hr. The solvent and excess reagent was removed under reduced pressure and the residue was triturated with hexanes. The mixture was centrifuged and the supernatant was removed. The residue was dried under reduced pressure to provide the product, docosahexaenoyl choline iodide (1.46 g, 96%), as an off white solid.

Workup

  1. customThe solvent and excess reagent was removed under reduced pressure
  2. customthe residue was triturated with hexanes
  3. customthe supernatant was removed
  4. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-a293ad9e71d64e2fa7d40639b215f019
Source dataset
uspto-grants-2000_11
Patent number
US06153653

Reaction notes

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