4-Nitrophenol → 1-Methyl-3-(4-nitro-phenoxymethyl)-piperidine

HRID 1442649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1442649
CC(C)([O-])C.[K+].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([O-:9])=[O:8].Cl.Cl[CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][N:22]([CH3:26])[CH2:21]1>CN(C=O)C.[OH-].[Na+]>[CH3:26][N:22]1[CH2:23][CH2:24][CH2:25][CH:20]([CH2:19][O:16][C:13]2[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=2)[CH2:21]1

Komponenten

6

Edukt 3

HCID 9804-NitrophenolHCID 1066903-Chloromethyl-1-methylpiperidinium chlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 219757981-Methyl-3-(4-nitro-phenoxymethyl)-piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1 M potassium t-butoxide (50.6 mL) was added dropwise to 4-nitrophenol Compound 35a (7.03 g, 50.6 mmol) in DMF (100 mL) at 0° C. After 20 mins, 3-chloromethyl-1-methylpiperidine hydrochloride Compound 35b (9.31 g, 50.6 mmol, neutralized prior to addition) in DMF (10 mL) was added to the reaction mixture. The reaction was then heated at 100° C. for 5 days. The cooled reaction was diluted with 1 N NaOH and washed with ethyl ether. The aqueous layer was then adjusted to pH 5 with NaH2PO4 and extracted with ethyl acetate. After drying over MgSO4, the organic layer was evaporated down to give 6.0 g of 1-methyl-3-(4-nitro-phenoxymethyl)-piperidine Compound 35c. Using the procedure of Example 1, Compound 35c was used in place of Compound 1n3 and carried forward to prepare 4-(1-methyl-piperidin-3-ylmethoxy)-phenylamine Compound 35d.

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. customThe cooled reaction
  3. washwashed with ethyl ether
  4. extractionextracted with ethyl acetate
  5. dry with materialAfter drying over MgSO4
  6. customthe organic layer was evaporated down

Quellen und Nachweise

ORD-Eintrag
ord-202384e78eaf4a7dbb512df593496dbe
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659284B2

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