Acetone → DL-Carnitine

HRID 325940Notes

Reaction equation

HRID 325940 reaction equation
Cl.[OH:2][CH:3]([CH2:9][C:10](=[O:12])[O-:11])[CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6].C(Cl)(=O)CC.CC(C)=O>FC(F)(F)C(O)=O>[OH:2][CH:3]([CH2:9][C:10](=[O:11])[O-:12])[CH2:4][N+:5]([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 180AcetoneHCID 62324Propionyl chlorideHCID 97941973-Hydroxy-4-(trimethylammonio)butanoate hydrochloride

Product 1

HCID 288DL-Carnitine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Carnitine hydrochloride (1.98 g; 0.01 moles) was dissolved in 5 cc of trifluoroacetic acid and to the solution propionyl chloride (1 cc; 0.01 moles) was added. The resulting solution was kept at 40°-45° C. overnight. The solution was then cooled to room temperature and acetone (50 cc) was added thereto keeping under stirring for 2 hours. The solid precipitate which formed (carnitine) was filtered off, 30 cc of ethyl ether were added to the filtrate and the resulting mixture was kept under stirring at 0° C. The solid precipitate which formed was filtered off and crystallized with ethanol-acetone-ethyl ether.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-71952d3015f54fd19f52968544c49aa7
Source dataset
uspto-grants-1984_04
Patent number
US04443475

Reaction notes

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