Reaktion #61999

Reaktionsgleichung

product

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

methyl-(2-pyridin-2-yl-ethyl)-amine

sodium triacetoxyborohydride

DCM

sodium hydroxide

→

ammonia DCM

Ausbeute 1.0%

title compound

Methyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-(2-pyridin-2-yl-ethyl)-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 the product of Example 9 (256 mg), methyl-(2-pyridin-2-yl-ethyl)-amine (143 mg), and acetic acid (0.06 mL) in DCM (4 mL) was treated with sodium triacetoxyborohydride (330 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (325 mg). 1H NMR (400 MHz, CDCl3): 8.51 (m, 1H), 7.57 (m, 1H), 7.18-7.12 (m, 3H), 7.10 (m, 1H), 6.82 (d, J=8.6 Hz, 2H), 3.98 (t, J=6.3 Hz, 2H), 3.49 (s, 2H), 2.99 (m, 2H), 2.78 (m, 2H), 2.46 (m, 2H), 2.39 (br, 4H), 2.25 (s, 3H), 1.96 (m, 2H), 1.61-1.54 (m, 4H), 1.47-1.40 (m, 2H).

Quelle