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

HRID 1064406

Reaktionsgleichung

Reaktionsgleichung von HRID 1064406
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 21973847N-[2-(1-benzylpiperidin-4-yl)ethyl]-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amineAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-02ff026e918e42f685948e624021ec16
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969722B2

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