Reaktion #71331

Reaktionsgleichung

1-Chloro-2-dimethylaminoethane hydrochloride

4-aminophenol

sodium hydroxide

→

title compound

Ausbeute 90.9%

4-(2-Dimethylamino-ethoxy)-phenylamine

Ausbeute 90.9%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe resulting dark suspension was filtered
2. 2
   workup.ADDITIONThe filtrate was diluted with DCM (200 ml)
3. 3
   Waschenwashed with brine (2×50 mL)
4. 4
   TrocknenThe organic phase was dried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigePurification of the residue by silica gel column chromatography (DCM/MeOH, 7:3)

Vorschrift

1-Chloro-2-dimethylaminoethane hydrochloride (2 g, 21.9 mmol, 1.2 equiv) was added in one portion to a mixture of 4-aminophenol (2 g, 18.3 mmol) and finely powdered sodium hydroxide (1.8 g, 45.8 mmol, 2.5 equiv) in DMF (27 mL), under an argon atmosphere. The reaction mixture was stirred for 17 h at rt. The resulting dark suspension was filtered. The filtrate was diluted with DCM (200 ml) and washed with brine (2×50 mL). The organic phase was dried (Na2SO4), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/MeOH, 7:3) provided 3 g of the title compound as a brown solid: API-MS: 181.2 [M+H]+; TLC: Rf=0.18 (DCM/MeOH, 7:3).

Quelle