تفاعل #11453

معادلة التفاعل

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

المردود 47.2%

المذيبات

diglyme

diglyme

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was heated
2. 2
   درجة الحرارةat reflux for 1.5 hours
3. 3
   تركيزconcentrated
4. 4
   أخرىto remove the diglyme (60° C. bath, 21 Pa)
5. 5
   أخرىThe residue was purified by column chromatography
6. 6
   غسيلeluting first with 1% methanol in dichloromethane
7. 7
   أخرىto remove residual diglyme
8. 8
   غسيلwith 5% methanol in dichloromethane to elute product
9. 9
   تركيزThe fractions were concentrated

الإجراء التجريبي

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.

المصدر