反応 #11452

反応方程式

4-(2-aminoethyl)-1-benzylpiperidine

2,4-dichloro-5,6-dimethyl-3-nitropyridine

triethylamine

→

N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine

収率 60.4%

溶媒

N,N-dimethylformamide

N,N-dimethylformamide

反応条件

後処理

1. 1
   濃縮it was concentrated under reduced pressure
2. 2
   その他The residue was partitioned between ethyl acetate and water
3. 3
   その他The layers were separated
4. 4
   抽出the aqueous layer was extracted with ethyl acetate
5. 5
   洗浄washed with brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他to provide an orange oil
9. 9
   その他The oil was purified by flash chromatography (400 mL silica gel eluting initially with 10% ethyl acetate in hexane

実験手順

A solution of 4-(2-aminoethyl)-1-benzylpiperidine (9.88 g, 45.2 mmol) in N,N-dimethylformamide was added dropwise to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (10.00 g, 45.2 mmol) and triethylamine (12.6 mL, 90.5 mmol) in N,N-dimethylformamide (320 mL). The reaction mixture was allowed to stir at ambient temperature for about 20 hours and then it was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organics were combined, washed with brine, dried over sodium sulfate and then concentrated under reduced pressure to provide an orange oil. The oil was purified by flash chromatography (400 mL silica gel eluting initially with 10% ethyl acetate in hexane, then with 15% ethyl acetate in hexane and finally with 40% ethyl acetate in hexane) to provide 11.00 g of N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine.

出典