Reaktion #45031

Reaktionsgleichung

Methyl 4-iodobenzoate

N,N-dimethylethane-1,2-diamine

caesium carbonate

2-acetylcyclohexanone

→

methyl 4-(2-[dimethylamino]ethylamino)benzoate

Ausbeute 99.1%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated
2. 2
   workup.DISSOLUTIONdissolved in methanol
3. 3
   Sonstigeabsorbed onto a SCX-2 cation exchange resin column
4. 4
   WaschenThe column was washed with methanol
5. 5
   Waschenthe product was eluted with 2M ammonia in methanol
6. 6
   SonstigeFractions were evaporated

Vorschrift

Methyl 4-iodobenzoate (1.19 g, 4.54 mmol, 1.0 eq) was dissolved in dry dimethylformamide (10 ml). N,N-dimethylethane-1,2-diamine (400 mg, 4.54 mmol, 1.0 eq), caesium carbonate (2.69 g, 9.08 mmol, 2.0 eq), 2-acetylcyclohexanone (120 μl, 0.908 mmol, 0.20 eq [20 mol %]) and copper (I) iodide (44 mg, 0.227 mmol, 0.05 eq [5 mol %]) were added and the mixture was stirred under nitrogen at 90° C. for 18 h. The reaction mixture was concentrated, dissolved in methanol and absorbed onto a SCX-2 cation exchange resin column. The column was washed with methanol and the product was eluted with 2M ammonia in methanol. Fractions were evaporated to give methyl 4-(2-[dimethylamino]ethylamino)benzoate (1.00 g, 99%) as a brown gum.

Quelle