Reaktion #9014

Reaktionsgleichung

(5-bromomethyl-2-cyano-phenyl) acetate

(1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

N,N-diisopropylethylamine

→

tan foam

Ausbeute 68.4%

2-Aminomethyl-5-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenol

Ausbeute 68.4%

Lösungsmittel

CH3CN

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated
2. 2
   Sonstigethe residue was partitioned between CH2Cl2 (40 mL) and brine (10 mL)
3. 3
   SonstigeThe phases were separated
4. 4
   Extraktionthe aqueous phase was extracted with CH2Cl2 (3×10 mL)
5. 5
   TrocknenThe combined organic extracts were dried (Na2SO4)
6. 6
   Einengenconcentrated
7. 7
   SonstigePurification of the crude material by column chromatography on silica gel (20:1 CH2Cl2—CH30H)

Vorschrift

To a solution of (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.375 g, 0.99 mmol) in CH3CN (5 mL) was added N,N-diisopropylethylamine (0.35 mL, 2.00 mmol) followed by a solution of (5-bromomethyl-2-cyano-phenyl) acetate (0.318 g, 1.25 mmol) in CH3CN (5 mL). The resultant mixture was heated to 60° C. for 15 hours then cooled to room temperature. The mixture was concentrated and the residue was partitioned between CH2Cl2 (40 mL) and brine (10 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (20:1 CH2Cl2—CH30H) followed by radial chromatography on silica gel (2 mm plate, 2:1 hexanes-EtOAc) provided 0.28 g (51%) of a tan foam.

Quelle