Réaction #3016

Équation de réaction

2,6-dimethoxy-4-methylaniline

formic acid

2-adamantanone

→

N-(2-adamantyl)-2,6-dimethoxy-4-methylaniline

Rendement 52.0%

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONis added dropwise at this temperature
2. 2
   TempératureThe reaction mixture is heated
3. 3
   Températureat reflux for 48 hours
4. 4
   Autreis then evaporated to dryness
5. 5
   FiltrationThe insoluble white crystals are filtered
6. 6
   ExtractionThe acidic filtrate is extracted with dichloromethane
7. 7
   LavageThe organic extracts are washed with a 5% aqueous sodium bicarbonate solution
8. 8
   Séchagewith water and the organic phases are then dried over anhydrous sodium sulphate
9. 9
   AutreEvaporation
10. 10
    Autreleaves a colourless residue which
11. 11
    Autreis purified by flash chromatography on a column of silica gel, eluent

Mode opératoire

2.1 g of 2,6-dimethoxy-4-methylaniline are dissolved in 10 ml of toluene, 0.5 ml of formic acid is then added to this solution and the mixture is heated to gentle reflux, under inert atmosphere, and 0.93 g of 2-adamantanone, dissolved in 10 ml of toluene, is added dropwise at this temperature. The reaction mixture is heated at reflux for 48 hours, is then evaporated to dryness and the residue is taken up in 30 ml of 2N hydrochloric acid. The insoluble white crystals are filtered and discarded. The acidic filtrate is extracted with dichloromethane. The organic extracts are washed with a 5% aqueous sodium bicarbonate solution and then with water and the organic phases are then dried over anhydrous sodium sulphate. Evaporation leaves a colourless residue which is purified by flash chromatography on a column of silica gel, eluent: toluene/ethyl acetate 7/3 (v/v) in order to obtain N-(2-adamantyl)-2,6-dimethoxy-4-methylaniline; M.p.=100° C., Yield 52%.

Source