Carnitine Chloride → DL-Carnitine

HRID 2252517Notes

Reaction equation

HRID 2252517 reaction equation
[CH3:1][N+:2]([CH2:5][CH:6]([OH:11])[CH2:7][C:8]([OH:10])=[O:9])([CH3:4])[CH3:3].[Cl-].[OH-].[Na+]>C(O)C>[OH:11][CH:6]([CH2:7][C:8](=[O:9])[O-:10])[CH2:5][N+:2]([CH3:4])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 5970Carnitine ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 288DL-Carnitine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of DL-carnitine hydrochloride (1.0 g, 5.05 mmol) and sodium hydroxide (0.303 g, 7.58 mmol) in ethanol (15 ml) was stirred at room temperature for 2 h. The formed white precipitate (NaCl) was removed by filtration, and the solvent was evaporated under reduced pressure to give a white solid, carnitine inner salt. A suspension of the carnitine inner salt and 1-iodooctadecane (2.31 g, 6.06 mmol) in DMF-dioxane (3:5, 40 ml) was heated with an oil-bath at 120° C. under Ar2 for 4 h. The solvent was removed by rotavapor and vacuum, and the residue was chromatographied with silica gel column using CH3OH—CH3Cl as eluant to give 2.22 g (81%) of stearyl carnitine ester as a white solid: 1H NMR (CDCl3) δ 4.79 (m, 1 H), 4.43 (d, J=5.3, 1H), 4.09 (t, J=6.9, 2H), 4.03 (d, J=13.0, 1H), 3.67 (dd, J=10.3, 13.3, 1H), 3.51 (s, 9H), 2.79 (dd, J=5.7, 17.0, 1H), 2.66 (dd, J=7.0, 17.1, 1H), 1.80-1.60 (m, 4H), 1.26 (broad s, 28H), 0.88 (t, J=6.6, 3H).

Workup

  1. customThe formed white precipitate (NaCl) was removed by filtration
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7bbe0f4e4f624857aba3c50d95f78c34
Source dataset
uspto-grants-2008_01
Patent number
US07323297B1

Reaction notes

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