Reaktion #315415

Reaktionsgleichung

3-methyl-piperidine

acetic acid

compound

6-(4-Formyl-phenoxy)-nicotinamide

sodium triacetoxyborohydride

6-(4-formyl-phenoxy)-nicotinamide

6-(4-Formyl-phenoxy)-nicotinamide

→

title compound

Ausbeute 29.5%

(±)-6-[4-(3-Methyl-piperidin-1-ylmethyl)-phenoxy]-nicotinamide

Ausbeute 29.5%

Lösungsmittel

1,2-dichloroethane

methanol

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprovides

Vorschrift

Using a method similar to Example 345, using 3-methyl-piperidine (0.0420 g, 0.423 mmol), 6-(4-formyl-phenoxy)-nicotinamide (compound of example 332, step 1) (0.101 g, 0.417 mmol), sodium triacetoxyborohydride (0.129 g, 0.610 mmol), and acetic acid (0.035 mL, 0.611 mmol) in 1,2-dichloroethane (8.0 mL) provides, after silica gel chromatography (10:1→7:3 methylene chloride:methanol), 0.0400 g (29%) of the title compound as a white foam: high resolution mass spectrum (electrospray): m/z calc for C19H24N3O2 326.1869, found 326.1841; 1H NMR (DMSO-d6): 8.66 (d, 1H, J=2.2 Hz), 8.29 (dd, 1H, J=2.5, 8.4 Hz), 8.06 (s b, 1H), 7.53 (s br, 1H), 7.38 (d, 2H, J=8.4 Hz), 7.17-7.09 (m, 3H), 3.38-3.28 (m, 2H), 2.83-2.70 (m, 2H), 1.95 (t, 1H, J=10.6 Hz), 1.74-1.41 (m, 5H), 0.97-0.79 (m, 4H).

Quelle