Reaktion #77722

Reaktionsgleichung

sodium cyanoborohydride

1-(4-methylbenzyl)-4-piperidinone

ammonium acetate

→

amine

Ausbeute 48.9%

1-(4-METHYLBENZYL)-4-PIPERIDINYLAMINE

Ausbeute 48.9%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring 16 hours
2. 2
   Filtrationfiltered
3. 3
   Sonstigethe methanol evaporated under vacuum
4. 4
   SonstigeThe residue was partitioned between ether and ice/HCl
5. 5
   ExtraktionThe acidic aqueous layer was extracted twice with ether
6. 6
   Extraktionextracted with CH2Cl2

Vorschrift

To 4.25 g (21 mmol) of 1-(4-methylbenzyl)-4-piperidinone 124 in 200 mL of anhydrous methanol was added 32.2 g (420 mmol) of ammonium acetate and 25 g of 3A molecular sieves. After stirring 30 min, 5.25 g (84 mmol) of sodium cyanoborohydride was added portionwise. After stirring 16 hours, the mixture was gravity filtered and the methanol evaporated under vacuum. The residue was partitioned between ether and ice/HCl. The acidic aqueous layer was extracted twice with ether, made basic with 50% aqueous NaOH and ice, and extracted with CH2Cl2 to give 2.1 g (48%) of the title amine 125 as a thick oil. GC/MS showed a molecular ion of 204. The product was used as is without further purification.

Quelle