Acetone → 1-[2-(2-Tert-butyl-5-nitro-phenoxy)-ethyl]-piperidine

HRID 238440

Reaktionsgleichung

Reaktionsgleichung von HRID 238440
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[OH:14])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].CC(C)=O.Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CCCC[N+](CCCC)(CCCC)CCCC.[I-].O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[O:14][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 11430Potassium Carbonate2×HCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride2×HCID 219596172-Tert-butyl-5-nitrophenol

Produkt 1

HCID 219595061-[2-(2-Tert-butyl-5-nitro-phenoxy)-ethyl]-piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To 2-tert-butyl-5-nitrophenol (1.01 g) and K2CO3 (1.72 g) was added acetone (35 ml) and H2O (10.5 mL), then 1-(2-chloroethyl)piperidine HCl (1.909 g) and TBAI (153 mg). The mixture was stirred at reflux overnight. Additional K2CO3 (850 mg) and 1-(2-chloroethyl)-piperidine HCl (950 mg) were added and the mixture was heated at reflux for 6 h. The mixture was concentrated in vacuo to an aqueous layer which was acidified with 2N HCl and extracted with EtOAc. The aqueous layer was basified with 6N NaOH and washed with CH2Cl2 (3×). The combined organic layers were washed with brine/1N NaOH and dried over Na2SO4. Washed the EtOAc layer with 2N NaOH/brine and dried over Na2SO4. The crude material was purified by silica gel column chromatography with 15% EtOAc/Hexanes to yield 1-[2-(2-tert-butyl-5-nitro-phenoxy)-ethyl]-piperidine as a light tan solid. (M+1)=307.3.

Aufarbeitung

  1. temperatureat reflux overnight
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 6 h
  4. concentrationThe mixture was concentrated in vacuo to an aqueous layer which
  5. extractionextracted with EtOAc
  6. washwashed with CH2Cl2 (3×)
  7. washThe combined organic layers were washed with brine/1N NaOH
  8. dry with materialdried over Na2SO4
  9. washWashed the EtOAc layer with 2N NaOH/brine
  10. dry with materialdried over Na2SO4
  11. customThe crude material was purified by silica gel column chromatography with 15% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bbeb3fbaa3e84d8a984ca8021263ab23
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642624B2

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