Reaktion #61982

Reaktionsgleichung

sodium hydroxide

4-(3-Pyrrolidin-1-yl-propoxy)-benzaldehyde

2-aminopyridine

sodium triacetoxyborohydride

DCM

→

ammonia DCM

Ausbeute 1.0%

title compound

Pyridin-2-yl-[4-(3-pyrrolidin-1-yl-propoxy)-benzyl]-amine

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with DCM (3×10 mL)
2. 2
   TrocknenThe combined organic phases were dried (sodium sulfate)
3. 3
   Sonstigeevaporated

Vorschrift

A solution of 4-(3-Pyrrolidin-1-yl-propoxy)-benzaldehyde (0.51 g), 2-aminopyridine (0.24 g), and acetic acid (0.13 mL) in DCM (7 mL) was treated with sodium triacetoxyborohydride (650 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (10 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-4% 2 M methanolic ammonia/DCM) gave the title compound as an off white solid (500 mg). 1H NMR (400 MHz, CDCl3): 8.09 (m, 1H), 7.39 (m, 1H), 7.26 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 6.58 (m, 1H), 6.36 (m, 1H), 4.79 (m, 1H), 4.41 (d, J=5.5, 2H), 4.01 (t, J=6.3 Hz, 2H), 2.63 (t, J=7.6 Hz, 2H), 2.54 (m, 4H), 2.04-1.96 (m, 2H), 1.79 (m, 4H).

Quelle