Reaktion #338365

Reaktionsgleichung

COMPOUND 249

Bis-(3-methyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine

Et3N

ethyl acetimidate hydrochloride

→

COMPOUND 338

Ausbeute 34.1%

[1-(1-imino-ethyl)-piperidin-4-yl]-bis-(3-methyl-pyridin-2-ylmethyl)-amine

Ausbeute 34.1%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthen concentrated
2. 2
   workup.ADDITIONSaturated NaHCO3 (15 mL) was added
3. 3
   Extraktionextracted with CH2Cl2 (2×40 mL)
4. 4
   SonstigePurification of the crude material by column chromatography on silica gel (15:1:1 CH2Cl2-MeOH—NH4OH)

Vorschrift

To a solution of COMPOUND 249 (0.1054 g, 0.34 mmol) in MeOH (4 mL) was added Et3N (0.1 mL, 0.68 mmol) and ethyl acetimidate hydrochloride (0.0549 g, 0.41 mmol), and stirred at room temperature for 24 hours then concentrated. Saturated NaHCO3 (15 mL) was added and extracted with CH2Cl2 (2×40 mL). Purification of the crude material by column chromatography on silica gel (15:1:1 CH2Cl2-MeOH—NH4OH) followed by radial chromatography on silica gel (50:3:2 CH2Cl2-MeOH—NH4OH) provided 0.0408 g (34%) of COMPOUND 338 as a white solid. 1H NMR (CDCl3) δ 1.60-1.72 (m, 2H), 1.90-1.95 (m, 2H), 2.09 (s, 6H), 2.12 (s, 3H), 2.47-2.68 (m, 4H), 3.82 (s, 4H), 4.17 (d, 2H, J=12.3 Hz), 7.06-7.10 (m, 2H), 7.37 (d, 2H, J=7.2 Hz), 8.34 (d, 2H, J=4.5 Hz). 13C NMR (CDCl3) δ 18.39, 23.92, 27.33, 45.64, 55.06, 57.89, 122.77, 133.81, 138.40, 146.29, 157.63, 164.64. ES-MS m/z 352.5 (M+H).

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