Reaktion #167221

Reaktionsgleichung

trans-1,2-diamino cyclohexane

potassium carbonate

1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

2-bromo naphthalene

→

1-(4-methyl-pyridin-3-yl)-3-naphthalen-2-yl-imidazolidin-2-one

Ausbeute 73.0%

Lösungsmittel

MeOH

1,4-Dioxane

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepreviously sparged with argon (10 minutes)
2. 2
   SonstigeThe reaction mixture was sparged with argon for a further 10 minutes
3. 3
   TemperaturThe resulting mixture was heated
4. 4
   FiltrationThe reaction mixture was filtered through a celite
5. 5
   Waschenthe bed was washed with chloroform
6. 6
   TrocknenThe organic layer was dried over Na2SO4
7. 7
   Einengenconcentrated
8. 8
   SonstigePurification by column chromatography (using silica gel of mesh size of 60-120, 1% MeOH in chloroform as eluent)

Vorschrift

Copper iodide (21.5 mg, 0.113 mmol), trans-1,2-diamino cyclohexane (0.041 mL, 0.339 mmol) and potassium carbonate (313 mg, 2.26 mmol) were added to 1,4-Dioxane (15 mL) previously sparged with argon (10 minutes). The reaction mixture was sparged with argon for a further 10 minutes, followed by the addition of 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 200 mg, 1.13 mmol) and 2-bromo naphthalene (234 mg, 1.13 mmol). The resulting mixture was heated to reflux at 110° C. for 15 hours. The reaction was monitored by TLC (10% MeOH in chloroform). The reaction mixture was filtered through a celite and the bed was washed with chloroform. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography (using silica gel of mesh size of 60-120, 1% MeOH in chloroform as eluent) afforded 250 mg (73% yield) of 1-(4-methyl-pyridin-3-yl)-3-naphthalen-2-yl-imidazolidin-2-one.

Quelle