Reaktion #450140

Reaktionsgleichung

N,N'-dicyclohexylcarbodiimide

2-(2-aminoethoxy)-1-phenylethanol

nicotinic acid

1-hydroxybenzotriazole

→

2-(2-nicotinoylamino-ethoxy)-1-phenylethanol

Ausbeute 23.6%

Lösungsmittel

triethylamine

ethyl acetate

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe insolubles were removed by filtration
2. 2
   workup.ADDITIONTo the filtrate was added 5 ml of water
3. 3
   SonstigeThe aqueous layer was separated
4. 4
   ExtraktionThe organic layer was extracted with 5 ml of water
5. 5
   workup.ADDITIONThe combined aqueous layer was mixed with 20 ml of chloroform
6. 6
   SonstigeThe organic layer was separated
7. 7
   Waschenwashed with water
8. 8
   Trocknendried over anhydrous magnesium sulfate
9. 9
   SonstigeThe solvent was removed by distillation under reduced pressure
10. 10
    SonstigeThe residue thus obtained
11. 11
    Sonstigewas purified by column chromatography (eluant: chloroform/ethanol=15/1)

Vorschrift

1.23 g of N,N'-dicyclohexylcarbodiimide was added, with ice cooling, to a solution of 1.08 g of 2-(2-aminoethoxy)-1-phenylethanol, 730 mg of nicotinic acid, 810 mg of 1-hydroxybenzotriazole and 0.83 ml of triethylamine dissolved in 5 ml of tetrahydrofuran. The resulting mixture was stirred at the same temperature for 5 minutes and further at room temperature for 1 hour. To the reaction mixture was added 11 ml of ethyl acetate. The insolubles were removed by filtration. To the filtrate was added 5 ml of water and the mixture was adjusted to pH 2 with 6N hydrochloric acid. The aqueous layer was separated. The organic layer was extracted with 5 ml of water. The extract was combined with the previously separated aqueous layer. The combined aqueous layer was mixed with 20 ml of chloroform and adjusted to pH 10 with potassium carbonate. The organic layer was separated, washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: chloroform/ethanol=15/1) to obtain 400 mg of oily 2-(2-nicotinoylamino-ethoxy)-1-phenylethanol (compound No. 216).

Quelle