Reaktion #61985

Reaktionsgleichung

product

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

benzyl-methyl-piperidin-4-yl-amine

sodium triacetoxyborohydride

DCM

sodium hydroxide

→

ammonia DCM

Ausbeute 1.0%

title compound

Benzyl-methyl-{1-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperidin-4-yl}-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 (155 mg), benzyl-methyl-piperidin-4-yl-amine (123 mg), and acetic acid (0.11 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (190 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 (155 mg). 1H NMR (400 MHz, CDCl3): 7.31-7.28 (m, 4H), 7.24-7.18 (m, 3H), 6.84 (d, J=8.8 Hz, 2H), 3.99 (t, J=6.3 Hz, 2H), 3.56 (s, 2H), 3.42 (s, 2H), 2.94 (m, 2H), 2.47 (m, 2H), 2.40 (m, 4H), 2.19 (s, 3H), 2.01-1.88 (m, 4H), 1.77 (m, 2H), 1.67 (m, 2H), 1.59 (m, 4H), 1.44 (m, 2H)

Quelle