Reaktion #61997

Reaktionsgleichung

product

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

1-(3-phenyl-allyl)-piperazine

sodium triacetoxyborohydride

DCM

sodium hydroxide

→

ammonia DCM

Ausbeute 1.0%

title compound

1-(3-Phenyl-allyl)-4-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperazine

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 (215 mg), 1-(3-phenyl-allyl)-piperazine (176 mg), and acetic acid (0.06 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (290 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 (303 mg). 1H NMR (400 MHz, CDCl3): 7.36 (m, 2H), 7.30 (m, 2H), 7.24-7.18 (m, 3H), 6.83 (d, J=8.6 Hz, 2H), 6.51 (d, J=15.9 Hz, 1H), 6.31-6.23 (m, 1H), 3.98 (t, J=6.3 Hz, 2H), 3.45 (s, 2H), 3.15 (m, 2H), 2.60-2.32 (m, 12H), 1.67 (br, 1H), 1.62-1.56 (m, 4H), 1.47-1.40 (m, 2H).

Quelle