Ammonium Acetate → 4-Amino-1-benzyl-3,5-dimethyl-3-ethylpiperidine

HRID 1865281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1865281
C([O-])(=O)C.[NH4+].[CH2:6]([N:13]1[CH2:18][CH:17]([CH3:19])[C:16](=O)[C:15]([CH3:23])([CH2:21][CH3:22])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([BH3-])#[N:25].[Na+]>CO>[NH2:25][CH:16]1[CH:17]([CH3:19])[CH2:18][N:13]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:14][C:15]1([CH3:23])[CH2:21][CH3:22]

Komponenten

5

Edukt 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 222788971-Benzyl-3,5-dimethyl-3-ethyl-4-piperidone

Produkt 1

HCID 102145914-Amino-1-benzyl-3,5-dimethyl-3-ethylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ammonium acetate (2.5 g, 32.46 mmol) was added to the stirred solution of 1-benzyl-3,5-dimethyl-3-ethyl-4-piperidone (3.0 g, 12.25 mmol) in methanol (40 ml) and stirring was continued for 20 hr at ambient temperature. The resulting mixture was cooled at 0° C. and sodium cyanoborohydride (0.8 g, 12.7 mmol) was added to it. Cooling was removed after 10 min. and resulting mixture was stirred for 20 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water, acidified with conc. HCl (pH 2) and extracted with ethyl acetate to remove impurities. The aqueous layer was basified with 1M sodium hydroxide solution (pH 9) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to furnish 4-amino-1-benzyl-3,5-dimethyl-3-ethylpiperidine.

Aufarbeitung

  1. temperatureCooling
  2. customwas removed after 10 min.
  3. customresulting mixture
  4. stirringwas stirred for 20 hr at ambient temperature
  5. concentrationThe reaction mixture was concentrated to dryness
  6. customtriturated with water
  7. extractionextracted with ethyl acetate
  8. customto remove impurities
  9. extractionextracted with ethyl acetate
  10. extractionEthyl acetate extract
  11. dry with materialwas dried (Na2SO4)
  12. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-be88d28b9d724099a75c27fb00573737
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07626032B2

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