Reaktion #2392111

Reaktionsgleichung

Methanol

iodine

sodium borohydride

2-(2-chlorophenyl)-N-methylacetamide

→

N-[2-(2-chlorophenyl)ethyl]-N-methylamine

Ausbeute 18.8%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturthe reaction mixture was heated
3. 3
   Temperaturto reflux for 16 hours
4. 4
   SonstigeThe solvent was removed in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in a mixture of tert-butyl methyl ether (200 ml)
6. 6
   SonstigeThe phases were separated
7. 7
   ExtraktionThe aqueous phase was extracted with tert-butyl methyl ether (2×100 ml)
8. 8
   TrocknenThe combined organic layers were dried over magnesium sulphate
9. 9
   SonstigeThe solvent was removed in vacuo
10. 10
    SonstigeThe crude product was purified by flash chromatography on silica (300 g)
11. 11
    workup.ADDITIONa mixture of DCM/methanol/25% aqueous ammonia (first: 100:10:1

Vorschrift

At 0° C., a solution of iodine (29.9 g, 0.12 mol) in THF (100 ml) was added dropwise to a suspension of sodium borohydride (11.1 g, 0.29 mol) and 2-(2-chlorophenyl)-N-methylacetamide (21.6 g, 0.12 mol) in THF (150 ml). After the addition was completed, the reaction mixture was heated to reflux for 16 hours. It was cooled to 0° C. Methanol (150 ml) was added dropwise. The solvent was removed in vacuo. The residue was dissolved in a mixture of tert-butyl methyl ether (200 ml) and a 20% aqueous solution of sodium hydroxide (200 ml). The phases were separated. The aqueous phase was extracted with tert-butyl methyl ether (2×100 ml). The combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (300 g), using a mixture of DCM/methanol/25% aqueous ammonia (first: 100:10:1, then: 100:20:2, then 100:30:3) as eluent, to give 3.82 g of N-[2-(2-chlorophenyl)ethyl]-N-methylamine.

Quelle