Ammonium Acetate → tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylate

HRID 40842

Reaktionsgleichung

Reaktionsgleichung von HRID 40842
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:23].[Na+]>CO.[OH-].[Na+]>[NH2:23][CH:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH3:2]

Komponenten

6

Edukt 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 22647295tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 4-acetylpiperidine-1-carboxylate (145 g, 0.64 mol) and ammonium acetate (225 g, 2.9 mol) in methanol (2 L) was stirred at room temperature for 1.5 hours. Sodium cyanoborohydride (30 g, 0.48 mol) was added in one portion and the stirring was continued overnight at room temperature. The reaction mixture was poured in 2N aq. NaOH (2 L) and extracted with dichloromethane (2×1 L). The combined extracts were washed with water (1 L), brine (0.3 L), and evaporated to dryness. The residue was dissolved in TBME (1.5 L), dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure. The residue was purified by bulb to bulb distillation at 180° C. and 0.1 mbar to afford the title compound as a colorless oil that partly solidified upon standing (131 g, 90% yield).

Aufarbeitung

  1. waitthe stirring was continued overnight at room temperature
  2. extractionextracted with dichloromethane (2×1 L)
  3. washThe combined extracts were washed with water (1 L), brine (0.3 L)
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in TBME (1.5 L)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure
  9. distillationThe residue was purified by bulb to bulb distillation at 180° C.

Quellen und Nachweise

ORD-Eintrag
ord-369371af84394b78a597fa75f03191d5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530489B2

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