Reaktion #433876

Reaktionsgleichung

1-aminohomopiperidine

101

(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine

NaOH

water

→

ammonium hydroxide

solid 152

Ausbeute 31.3%

N-Azepan-yl-6-chloro-N′-(3-chloro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine

Ausbeute 31.3%

Lösungsmittel

acetone

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux overnight under nitrogen
2. 2
   ExtraktionThe reaction mixture was extracted 3 times with dichloromethane
3. 3
   Waschenthe combined organic layers were washed with brine
4. 4
   Trocknendried over potassium carbonate
5. 5
   EinengenThe sample was concentrated on a rotary evaporator
6. 6
   Sonstigethe resulting oil was dried overnight under vacuum

Vorschrift

To 101 (6.03 g, 20.0 mmol) dissolved in acetone (75 mL) was added a solution of 1-aminohomopiperidine (2.3 mL, 20.0 mmol) in acetone (10 mL) followed by addition of NaOH (8.0 mL 2.5 N NaOH solution, 20.0 mmol) and 20 mL of water. The reaction mixture was allowed to stir at reflux overnight under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was concentrated on a rotary evaporator and the resulting oil was dried overnight under vacuum. Column chromatography (96:3:1 dichloromethane: methanol: conc. ammonium hydroxide) yielded a light purple solid 152 (1.2 g, 16%), mp 139° C.; TLC (silica gel, 96:3:1, CH2Cl2, CH3OH, conc. NH4OH), Rf 0.31; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 52.5 min, 94.9% purity; MS (ESI): m/z 383 (M+H, 100).

Quelle