Reaktion #1602362

Reaktionsgleichung

HCl

2-chloro-4-phenylquinazoline

tert-butyl 4-aminopiperidine-1-carboxylate

→

4-phenyl-N-(piperidine-4-yl)quinazolin-2-amine

Ausbeute 117.1%

Lösungsmittel

n-butanol

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter removal of the n-butanol
2. 2
   Sonstigeon a rotary evaporator, dichloromethane (100 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   Sonstigethe suspension was sonicated for 30 min
5. 5
   Filtrationfiltered
6. 6
   EinengenThe solution was then concentrated on a rotary evaporator
7. 7
   Sonstigeto give a brown residue
8. 8
   SonstigeThis residue was purified by column chromatography on silica gel (95:5 hexanes/ethyl acetate)
9. 9
   Sonstigeto yield a green oil that
10. 10
    SonstigeThe solvent was removed on a rotary evaporator

Vorschrift

A solution of 2-chloro-4-phenylquinazoline (1.38 g, 5.75 mmol), and tert-butyl 4-aminopiperidine-1-carboxylate (2.81 g, 14.1 mmol) was heated at reflux in n-butanol (20 mL) for 4 h. After removal of the n-butanol on a rotary evaporator, dichloromethane (100 mL) was added and the suspension was sonicated for 30 min and filtered. The solution was then concentrated on a rotary evaporator to give a brown residue. This residue was purified by column chromatography on silica gel (95:5 hexanes/ethyl acetate) to yield a green oil that was treated with 4M HCl in 1,4-dioxane (100 mL) at 100° C. for 1 h. The solvent was removed on a rotary evaporator to give 4-phenyl-N-(piperidine-4-yl)quinazolin-2-amine (2.05 g, 90%) as a dark yellow solid.

Quelle