Diethyl Ether → p-Methoxy cinnamoyl carnitine hydrochloride

HRID 435476Notes

Reaction equation

HRID 435476 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].[CH3:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][C:21]([Cl:23])=[O:22])=[CH:17][CH:16]=1.CCOCC>C(O)(C(F)(F)F)=O.CC(C)=O>[ClH:23].[CH3:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][C:21]([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:17][CH:16]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 97941973-Hydroxy-4-(trimethylammonio)butanoate hydrochlorideHCID 534017724-Methoxycinnamic acid chloride

Product 1

HCID 131713071p-Methoxy cinnamoyl carnitine hydrochlorideYield 70%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

7.12 g (0.036 moles) of carnitine hydrochloride are dissolved in 12 mls of CF3COOH, and to the solution an excess (25 mls) of p-methoxy cinnamoyl chloride is added and the mixture kept under stirring at 40°-50° C. for 4-5 hours. At the end of this period of time the mixture is diluted with 90 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; 9 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-ba46034d2ac74f54af06357aa4711566
Source dataset
uspto-grants-1983_08
Patent number
US04401827

Reaction notes

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