tert-Butanol → 1-Benzyl-4-(N-Boc-amino)piperidine

HRID 555353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555353
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C)(C)C.[C:20]([O:24][C:25](OC([O-])=O)=[O:26])([CH3:23])([CH3:22])[CH3:21]>[OH-].[Na+]>[C:20]([O:24][C:25](=[O:26])[NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)([CH3:23])([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 6386tert-ButanolHCID 4158521-Benzyl-4-piperidylamineHCID 22064466Tert-butyldicarbonate

Produkt 1

HCID 44386181-Benzyl-4-(N-Boc-amino)piperidineAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

1-Benzylpiperidin-4-ylamine (3 g, 15.8 mmol) was dissolved in 1M aqueous sodium hydroxide solution (35.8 ml) and t-butanol (32 ml) in a 250 ml vessel, and t-butyl-dicarbonate ((t-Boc)2O; 3.79 g, 17.38 mmol) was added thereto while stirring. The resulting mixture was reacted at room temperature for 12 hrs. After the completion of reaction, the reaction mixture was extracted with ethyl acetate twice. The organic layer was separated, washed with 0.1N hydrochloric acid solution and brine in order, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 3.80 g of the title compound as a white solid (yield 82.8%).

Aufarbeitung

  1. customThe resulting mixture was reacted at room temperature for 12 hrs
  2. customAfter the completion of reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate twice
  4. customThe organic layer was separated
  5. washwashed with 0.1N hydrochloric acid solution and brine in order
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-040d32411aa241908b09b492c50f7232
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053435B2

Notizen zur Reaktion

Wird geladen…