Methyl Chloride → Farnesylacetylaminoethyltrimethylammonium chloride

HRID 1659294Notes

Reaction equation

HRID 1659294 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][NH:5][C:6](=[O:23])[CH2:7][CH2:8][CH:9]=[C:10]([CH2:12][CH2:13][CH:14]=[C:15]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH3:16])[CH3:11].[CH3:25][Cl:26]>C(#N)C>[Cl-:26].[CH2:8]([CH2:7][C:6]([NH:5][CH2:4][CH2:3][N+:2]([CH3:25])([CH3:1])[CH3:24])=[O:23])[CH:9]=[C:10]([CH2:12][CH2:13][CH:14]=[C:15]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH3:16])[CH3:11]

Participants

4

Reactant 2

HCID 6327Methyl ChlorideHCID 57227551N,N-dimethyl-N'-farnesylacetylethylenediamine

Product 1

HCID 86738135Farnesylacetylaminoethyltrimethylammonium chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A three-necked flask equipped with a thermometer, a reflux condenser and a gas inlet tube was charged with 10 g of N,N-dimethyl-N'-farnesylacetylethylenediamine prepared by the procedure of Example 1 and 100 ml of acetonitrile. The contents were refluxed for 6 hours while methyl chloride was introduced. Thereafter, the methyl chloride and acetonitrile were distilled off and the remaining product was purified by column chromatography to give 8.6 g of farnesylacetylaminoethyltrimethylammonium chloride. The product was identified by proton NMR and elemental analysis. The NMR data were as follows:

Workup

  1. customA three-necked flask equipped with a thermometer, a reflux condenser and a gas inlet tube
  2. additionwas introduced
  3. distillationThereafter, the methyl chloride and acetonitrile were distilled off
  4. customthe remaining product was purified by column chromatography

Sources & evidence

ORD record
ord-6c7f63834ef649ed89b70b47bcc3c6c6
Source dataset
uspto-grants-1981_12
Patent number
US04303588

Reaction notes

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