Sodium Hydroxide → N,N-dimethyl-N'-farnesylacetylethylenediamine

HRID 1659293Notes

Reaction equation

HRID 1659293 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[CH2:7]([CH2:22][C:23](Cl)=[O:24])[CH:8]=[C:9]([CH2:11][CH2:12][CH:13]=[C:14]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH3:15])[CH3:10].[OH-].[Na+]>CCOCC>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:23](=[O:24])[CH2:22][CH2:7][CH:8]=[C:9]([CH2:11][CH2:12][CH:13]=[C:14]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH3:15])[CH3:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66053N,N-DimethylethylenediamineHCID 54440908Farnesylacetyl chloride

Product 1

HCID 57227551N,N-dimethyl-N'-farnesylacetylethylenediamineYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 12.3 g of N,N-dimethylethylenediamine in 50 cc of ether was placed in a three-necked flask equipped with a stirrer, a dropping funnel and a thermometer. Then 37 g of the above-mentioned farnesylacetyl chloride was added dropwise at 5° to 10° C. After completion of the dropping, the reaction was continued at room temperature for an hour. After the reaction, 70 g of a 10% aqueous solution of sodium hydroxide was added, the aqueous layer was separated from the ether layer and extracted with ether, and the ether extract was combined with the ether layer. The ether was distilled off from the ether solution. The residue was subjected to preparative liquid chromatography (Waters Associates, Prep LC/System 500), which gave 38.5 g of N,N-dimethyl-N'-farnesylacetylethylenediamine (1). The structure was identified by proton NMR and mass spectrometry (M.S.). The NMR data are shown below.

Workup

  1. customequipped with a stirrer, a dropping funnel
  2. waitAfter completion of the dropping, the reaction was continued at room temperature for an hour
  3. additionwas added
  4. customthe aqueous layer was separated from the ether layer
  5. extractionextracted with ether
  6. extractionthe ether extract
  7. distillationThe ether was distilled off from the ether solution

Sources & evidence

ORD record
ord-cba8e6f4a3d94a3d8ead912ef138358d
Source dataset
uspto-grants-1981_12
Patent number
US04303588

Reaction notes

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