2-Pyridineethanamine → N1-geranyl-N2-(2-(pyridin-2-yl)ethyl)oxalamide

HRID 1260129Notes

Reaction equation

HRID 1260129 reaction equation
[CH3:1][C:2]([CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:3][CH2:4][NH:5][C:6](=[O:12])[C:7]([O:9]CC)=O.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][NH2:27]>C(O)C>[CH2:4]([NH:5][C:6](=[O:12])[C:7]([NH:27][CH2:26][CH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=1)=[O:9])/[CH:3]=[C:2](/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:17])[CH3:18])\[CH3:1]

Participants

4

Reactant 2

HCID 759192-PyridineethanamineHCID 72265544Ethyl 2-(3,7-dimethylocta-2,6-dienylamino)-2-oxoacetate

Product 1

HCID 53344994N1-geranyl-N2-(2-(pyridin-2-yl)ethyl)oxalamideYield 66.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ethyl 2-(3,7-dimethylocta-2,6-dienylamino)-2-oxoacetate (1.5 g, 5.92 mmol) was mixed with 2-(pyridin-2-yl)ethanamine (1 g, 8.19 mmol) in ethanol (20 ml) to give a yellow solution. The reaction mixture was stirred at reflux for 1.5 hour. Then the solvent was removed by evaporation. The remaining residual solid was washed with ethanol/pentane to provide the target compound as white crystals (1.3 g; 65% yield). The product is ca. 97% pure according to NMR analysis.

Workup

  1. customto give a yellow solution
  2. temperatureat reflux for 1.5 hour
  3. customThen the solvent was removed by evaporation
  4. washThe remaining residual solid was washed with ethanol/pentane

Sources & evidence

ORD record
ord-be09ac18fd8d417cbe004d98004cf9dd
Source dataset
uspto-grants-2013_06
Patent number
US08470384B2

Reaction notes

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