Hydrochloric Acid → N-(2-methoxyphenyl)piperidin-4-amine

HRID 1784702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1784702
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO.C(OCC)(=O)C>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 22557919tert-Butyl 4-((2-methoxyphenyl)amino)piperidine-1-carboxylate

Produkt 1

HCID 10584422N-(2-methoxyphenyl)piperidin-4-amineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-methoxyphenylamino)-piperidine-1-carboxylic acid tert-butyl ester (2.7 g, 8.8 mmol) in methanol (30 mL) was added 4N hydrochloric acid in ethyl acetate (20 mL) at room temperature. After stirring for 1 h, the resulting suspension was concentrated in vacuo. The residue was partitioned between chloroform and 1N sodium hydroxide. The aqueous layer was extracted with chloroform. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting 10-20% methanol in chloroform to furnish 4-(2-methoxyphenylamino)-piperidine (1.8 g, 8.7 mmol, 99%) as white crystals.

Aufarbeitung

  1. concentrationthe resulting suspension was concentrated in vacuo
  2. customThe residue was partitioned between chloroform and 1N sodium hydroxide
  3. extractionThe aqueous layer was extracted with chloroform
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting 10-20% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-0ecb189bad7f45de80b6db393d2d5e90
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504411B2

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