ChemicalBook CAS DataBase List phosphorylcholine

phosphorylcholine synthesis

4synthesis methods

Product Name:phosphorylcholine
CAS Number:107-73-3
Molecular formula:C5H15ClNO4P
Molecular Weight:219.6

Phosphorylcholine was synthesised from choline chloride and phosphorus pentoxide, the solvent being 100 percent. phosphoric acid [phosphorylation method of Manaka, 1931]. 2.4 g choline chloride, dried over phosphorus pentoxide, were dissolved in 15 g. 100 per cent. phosphoric acid, the solution was heated at 70°C. in vacuo until evolution of HC1 ceased, and 5 g. phosphorus pentoxide were added. The mixture, which became homogeneous after a few minutes, was kept at 70°C. for 3 hours. The clear viscous solution was poured into 400c.c. of ice water, and a barium hydroxide solution, saturated at 50°C., was added until the solution showed a strongly alkaline reaction. At the end of the neutralisation a smell of trimethylamine appears. The barium phosphate was centrifuged, the excess of barium ions removed by carbon dioxide, the precipitate centrifuged, and the solution reduced in vacuo to a small volume. It still contained a certain amount of barium ions depending on the amount of negatively charged phosphorylcholine ions present. The latter is determined by the pH of the solution. The amount of barium ions present was determined in an aliquot part of the solution by precipitation with sulphuric acid, and the amount of n-sulphuric acid required for complete precipitation of the barium ions added.

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Yield:107-73-3 95%

Reaction Conditions:

Stage #1: phosphorylcholine chloride, calcium saltwith oxalic acid in water at 50; for 2 h;
Stage #2: with ethylenediaminetetraacetic acid in water;

Steps:

1

Example 1 : Preparation of phosphocholine chloride (3)lOOg of calcium 2-(trimethylammonio)ethylphosphate chloride tetrahydrate(Chinese, Chem-Sourcing product; 1 equivalent, 303.2 mmol) was dissolved in 350ml of water and heated at 50 ^°C . Then, 6Og of oxalic acid (1.5 equivalent, 475.9 mmol) was added thereto and shaken for 2 hours. When the weight % of calcium became to less than 0.1%, the reaction was completed by using the EDTA (ethylenediaminetetraacetic acid). Then, the filtrate was collected by filtering and decompressed for concentration. The obtained product was dissolved in 10OmL of ethanol, and the phosphocholine chloride was obtained by decompressed concentration (63.27g, yield 95%). ¹H NMR (D₂O, 300MHz): δ 3.09 (s, 9H), 3.54 (m, 2H), 4.18 (m, 2H).

References:

WO2007/145476,2007,A1 Location in patent:Page/Page column 9

67-48-1 Synthesis