반응 #11453

반응 방정식

Sodium hydride

phenol

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

phenoxide

→

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

수율 47.2%

용매

diglyme

diglyme

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux for 1.5 hours
3. 3
   농축concentrated
4. 4
   기타to remove the diglyme (60° C. bath, 21 Pa)
5. 5
   기타The residue was purified by column chromatography
6. 6
   세척eluting first with 1% methanol in dichloromethane
7. 7
   기타to remove residual diglyme
8. 8
   세척with 5% methanol in dichloromethane to elute product
9. 9
   농축The fractions were concentrated

실험 절차

Sodium hydride (1.196 g of 60%, 29.9 mmol) was added to a solution of phenol (2.81 g, 29.9 mol) in diglyme (40 mL). The mixture was stirred for 15 minutes after the cessation of gas evolution. A solution of N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine (10.9 g, 27.2 mmol) in hot diglyme was added to the phenoxide mixture. The reaction mixture was heated at reflux for 1.5 hours, cooled to ambient temperature, and then concentrated to remove the diglyme (60° C. bath, 21 Pa). The residue was purified by column chromatography eluting first with 1% methanol in dichloromethane to remove residual diglyme and then with 5% methanol in dichloromethane to elute product. The fractions were concentrated to provide 5.91 g of N-[2-(1-benzylpiperidin-4-yl)ethyl]-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amine as an orange-brown oil which solidified on standing.

출처