Reaktion #360059

Reaktionsgleichung

4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde

piperidine

→

NH3

title compound

Ausbeute 58.6%

1-{4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}piperidine

Ausbeute 58.6%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe isolated waxy solid was purified by column chromatography on silica eluting with a gradient of DCM

Vorschrift

4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde (272 mg, 0.86 mmol), piperidine (0.161 mL, 1.63 mmol), absolute ethanol (11 mL), activated 4 Å molecular sieves, titanium (IV) isopropoxide (1.205 mL, 4.28 mmol) and STAB (1.54 g, 7.28 mmol) were reacted in accordance with the general procedure D. The isolated waxy solid was purified by column chromatography on silica eluting with a gradient of DCM:MeOH:NH3 (from 99:0:1 to 90:9:1) to give the title compound (97.4 mg, 25%). 1H NMR (400 MHz, CDCl3) δ 7.21 (d, 2H), 6.85 (d, 2H), 4.02 (t, 2H), 3.77-3.72 (m, 2H), 3.54-3.48 (t, 2H), 2.63 (t, 2H), 2.53 (m, 4H), 2.29 (s, 2H), 2.13-1.87 (m, 10H), 1.79 (quint, 4H), 1.41-1.36 (m, 4H), 1.30-1.26 (m, 2H).

Quelle