Reaktion #544135

Reaktionsgleichung

sodium hydroxide

product

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

1-piperidin-4-yl-2,3-dihydro-1H-indole

sodium triacetoxyborohydride

DCM

→

ammonia DCM

Ausbeute 1.0%

title compound

1-{1-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-piperidin-4-yl}-2,3-dihydro-1H-indole

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 (112 mg) and 1-piperidin-4-yl-2,3-dihydro-1H-indole*2TFA (194 mg) in DCM (2 mL) was treated with sodium triacetoxyborohydride (150 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 (78 mg). 1H NMR (400 MHz, CDCl3): 7.22 (d, J=8.6 Hz, 2H), 7.06–7.00 (m, 2H), 6.85 (d, J=8.6 Hz, 2H), 6.59 (t, J=7.1 Hz, 1H), 6.39(d, J=7.8 Hz, 1H), 4.00 (t, J=6.3 Hz, 2H), 3.48 (s, 2H), 3.41–3.32 (m, 3H), 2.99 (m, 2H), 2.93 (t, J=8.3 Hz, 2H), 2.54 (m, 2H), 2.47 (br, 4H), 2.09–1.98 (m, 4H), 1.79–1.70 (m, 4H), 1.67–1.61 (m, 4H), 1.50–1.43 (m, 2H).

Quelle