Reaktion #61986

Reaktionsgleichung

product

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

dimethylamine hydrochloride

sodium triacetoxyborohydride

DCE

sodium hydroxide

→

ammonia DCM

Ausbeute 3.0%

title compound

Dimethyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amine

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

A solution of the product of Example 9 (175 mg), dimethylamine hydrochloride (64 mg), and acetic acid (0.05 mL) in DCE (3 mL) was treated with sodium triacetoxyborohydride (210 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (1 mL) and extracted with DCM (3×3 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. Chromatography of the residue (3% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (70 mg). 1H NMR (400 MHz, CDCl3): 7.19 (d, J=8.6 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 3.99 (t, J=6.4 Hz, 2H), 3.35 (s, 2H), 2.50-2.35 (m, 6H), 2.22 (s, 6H), 2.01-1.94 (m, 2H), 1.63-1.55 (m, 4H), 1.46-1.40 (m, 2H).

Quelle