Ammonium Acetate → 1-(4-Aminopiperidin-1-yl)-3-phenylpropan-1-one

HRID 49446

Reaktionsgleichung

Reaktionsgleichung von HRID 49446
[C:1]1([CH2:7][CH2:8][C:9]([N:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:24].[Na+]>CO>[C:1]1([CH2:7][CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([NH2:24])[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 178176121-(3-Phenylpropionyl)-4-ketopiperidine

Produkt 1

HCID 167937721-(4-Aminopiperidin-1-yl)-3-phenylpropan-1-oneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 3.2 g (13.8 mmol) of 135 in 125 mL of anhydrous methanol was added 21.3 g of ammonium acetate and 20 g of 3A molecular sieves. After stirring 30 min, 3.47 g (55.2 mmol) of sodium cyanoborohydride was added portionwise with stirring. After 3 hours, the mixture was gravity filtered, and the methanol evaporated under vacuum. The residue was partitioned between ice/HCl and ether. The acidic aqueous phase was extracted twice more with ether. The aqueous phase was made basic with ice and 50% aqueous NaOH. The mixture was extracted with CH2Cl2, dried, and evaporated under vacuum to give 1.5 g (47%) of the title amine 136. GC/MS indicated 100% purity with a molecular ion of 232.

Aufarbeitung

  1. stirringwith stirring
  2. waitAfter 3 hours
  3. filtrationfiltered
  4. customthe methanol evaporated under vacuum
  5. customThe residue was partitioned between ice/HCl and ether
  6. extractionThe acidic aqueous phase was extracted twice more with ether
  7. extractionThe mixture was extracted with CH2Cl2
  8. customdried
  9. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-08ae6f502bb042ebb1e5e2dd2d00758b
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706740B2

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