反応 #806595

反応方程式

1-aminohomopiperidine

101

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

NaOH

water

→

solid 152

収率 31.3%

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

収率 31.3%

ammonium hydroxide

溶媒

acetone

acetone

反応条件

後処理

1. 1
   温度at reflux overnight under nitrogen
2. 2
   抽出The reaction mixture was extracted 3 times with dichloromethane
3. 3
   洗浄the combined organic layers were washed with brine
4. 4
   乾燥dried over potassium carbonate
5. 5
   濃縮The sample was concentrated on a rotary evaporator
6. 6
   その他the resulting oil was dried overnight under vacuum

実験手順

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).

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