Reaktion #45145

Reaktionsgleichung

1-Methyl-1,4-diazepane

methyl 4-fluorobenzoate

→

methyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate

Ausbeute 24.1%

Lösungsmittel

DMA

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was evaporated
2. 2
   Sonstigequenched with 2M sodium hydroxide (50 ml)
3. 3
   ExtraktionThis was extracted with DCM (3×50 ml)
4. 4
   WaschenThe combined organic extracts were washed with saturated brine (50 ml)
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated to dryness
8. 8
   SonstigeThe crude product was purified by silica column chromatography
9. 9
   Wascheneluting with a gradient of 0 to 10% MeOH in DCM
10. 10
    SonstigePure fractions were evaporated to dryness

Vorschrift

1-Methyl-1,4-diazepane (15.07 g, 132.00 mmol) was added to methyl 4-fluorobenzoate (7.76 mL, 60 mmol) in DMA (150 mL). The resulting solution was stirred at 100° C. for 40 h. The reaction mixture was evaporated and quenched with 2M sodium hydroxide (50 ml). This was extracted with DCM (3×50 ml). The combined organic extracts were washed with saturated brine (50 ml), dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate (3.59 g, 24.10%) as a tan waxy solid.

Quelle