Reaktion #745433

Reaktionsgleichung

3,5-bis(3-methoxypropyl)benzoic acid

cyclopropanamine

o-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate

triethylamine

→

title compound

N-Cyclopropyl-3,5-bis(3-methoxypropyl)benzamide

Lösungsmittel

EtOAc

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe organic extract
2. 2
   Waschenwas washed with 10% aqueous HCl solution, brine
3. 3
   Trocknendried over MgSO4
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe crude product was purified by flash column chromatography (SiO2, 50%→>70% EtOAc in Hex)

Vorschrift

To a solution of 3,5-bis(3-methoxypropyl)benzoic acid (1 eq.) from the previous step in DCM (0.1 M) was added cyclopropanamine (1.3 eq.), o-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (aka. HATU, 1.5 eq.), and triethylamine (3 eq.). After stirring at rt for 18 h, the reaction was diluted with EtOAc. The organic extract was washed with 10% aqueous HCl solution, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 50%→>70% EtOAc in Hex) to afford the title compound as an oil.

Quelle