Reaktion #61990

Reaktionsgleichung

sodium hydroxide

product

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

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

TFA

sodium triacetoxyborohydride

DCM

→

ammonia DCM

Ausbeute 1.0%

title compound

5-Bromo-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 (93 mg) and 5-bromo-1-piperidin-4-yl-2,3-dihydro-1H-indole*2 TFA (191 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 (79 mg). 1H NMR (400 MHz, CDCl3): 7.20 (d, J=8.6 Hz, 2H), 7.11-7.07 (m, 2H), 6.84 (d, J=8.6 Hz, 2H), 6.23 (d, J=9.1 Hz, 1H), 4.00 (t, J=6.1 Hz, 2H), 3.46 (s, 2H), 3.37 (7, J=8.3 Hz, 2H), 3.28 (m, 1H), 2.97 (m, 2H), 2.90 (t, J=8.3 Hz, 2H), 2.54 (m, 2H), 2.47 (br, 4H), 2.06-1.97 (m, 4H), 1.75-1.60 (m, 8H), 1.50-1.43 (m, 2H).

Quelle