Diethyl Ether → Cinnamoyl carnitine hydrochloride

HRID 435475Notes

Reaction equation

HRID 435475 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:13]([Cl:23])(=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCOCC>C(O)(C(F)(F)F)=O.CC(C)=O>[ClH:23].[C:13]([C:3]([CH2:9][C:10](=[O:11])[O-:12])([CH2:4][N+:5]([CH3:8])([CH3:6])[CH3:7])[OH:2])(=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 660233-Phenylprop-2-enoyl chlorideHCID 97941973-Hydroxy-4-(trimethylammonio)butanoate hydrochloride

Product 1

HCID 131713069Cinnamoyl carnitine hydrochlorideYield 70%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4.55 g (0.023 moles) of carnitine hydrochloride are dissolved in 6.9 mls of CF3COOH, and to the solution an excess (16 mls) of cinnamoyl chloride is added. The mixture is kept under stirring at 40°-45° C. for 4-5 hours. At the end of this period of time, the mixture is diluted with 60 mls of acetone and some ether is slowly added till complete precipitation. The mixture is filtered and the precipitate which has the tendency to become hygroscopic is quickly washed with ether and dried under vacuum at a temperature not exceeding 50° C.; 5.3 g of a product are obtained (yield 70%) having the following characteristics:

Workup

  1. filtrationThe mixture is filtered
  2. washis quickly washed with ether
  3. customdried under vacuum at a temperature not
  4. customexceeding 50° C.

Sources & evidence

ORD record
ord-f0497f1aa60a4845b3dc8e451c561c50
Source dataset
uspto-grants-1983_08
Patent number
US04401827

Reaction notes

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