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

HRID 1265067

반응식

HRID 1265067 반응식
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][NH:25][C:26]2[C:31]([CH3:32])=[C:30]([CH3:33])[N:29]=[C:28](Cl)[C:27]=2[N+:35]([O-:37])=[O:36])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[O-]C1C=CC=CC=1>COCCOCCOC>[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][NH:25][C:26]2[C:27]([N+:35]([O-:37])=[O:36])=[C:28]([O:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[N:29]=[C:30]([CH3:33])[C:31]=2[CH3:32])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 119047PhenolateHCID 21973806N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine

생성물 1

HCID 21973847N-[2-(1-benzylpiperidin-4-yl)ethyl]-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amine수율 47.2%

시약·촉매·용매 1

HCID 8150Diglyme용매2회

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.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationconcentrated
  4. customto remove the diglyme (60° C. bath, 21 Pa)
  5. customThe residue was purified by column chromatography
  6. washeluting first with 1% methanol in dichloromethane
  7. customto remove residual diglyme
  8. washwith 5% methanol in dichloromethane to elute product
  9. concentrationThe fractions were concentrated

출처 및 근거

ORD 기록
ord-cff93dc3c9d840bf8a201c836dfd8df3
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06545017B1

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