Reaktion #62047

Reaktionsgleichung

sodium triacetoxyborohydride

NH4Cl EtOAc

4-(dimethylamino)benzaldehyde

4-isopropylaniline

→

title compound

N-[4-(Dimethylamino)benzyl]-4-isopropylaniline

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction
2. 2
   workup.ADDITIONthis mixture was poured into a separatory funnel
3. 3
   WaschenThe organic layer was washed with brine
4. 4
   Trocknendried over anhydrous Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe crude material was further purified by flash chromatography
8. 8
   Wascheneluting with a gradient from 100% hexanes to 10% EtOAc/hexanes

Vorschrift

To a 0.33 M solution of 4-(dimethylamino)benzaldehyde in THF at 0° C. was added 1.1 equiv of 4-isopropylaniline followed by 1.5 equiv of sodium triacetoxyborohydride. After allowing the reaction to warm to room temperature overnight, this mixture was poured into a separatory funnel containing aqueous NH4Cl/EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude material was further purified by flash chromatography, eluting with a gradient from 100% hexanes to 10% EtOAc/hexanes to provide the title compound as a white solid.

Quelle