Reaktion #91473

Reaktionsgleichung

4-phenylpiperidine

EDCI

HOBt

NMM

3,4,5-trimethoxybenzoic acid

→

compound 1g

(4-Phenylpiperidin-1-yl)(3,4,5-trimethoxyphenyl)methanone

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschensequentially washed with water
2. 2
   TrocknenNaHCO3, brine and dried over MgSO4
3. 3
   SonstigeThe solvent was removed under reduced pressure
4. 4
   Sonstigeto yield a crude product, which
5. 5
   Sonstigewas purified by column chromatography

Vorschrift

To a mixture of 4-phenylpiperidine 41g (5 mmol), EDCI (6 mmol), HOBt (5.5 mmol) and NMM (6 mmol) in CH2Cl2 (50 mL) was added 3,4,5-trimethoxybenzoic acid (5.3 mmol) and stirring continued at RT for overnight. The reaction mixture was diluted with CH2Cl2 (100 mL) and sequentially washed with water, satd. NaHCO3, brine and dried over MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure compound 1g. (57.9%). 1H NMR (CDCl3) δ 7.35-7.21 (m, 5H), 6.66 (s, 2H), 4.84 (br, 1H), 3.95 (br, 1H), 3.88 (s, 6H), 3.86 (s, 3H), 3.20-2.87 (br, 2H), 2.85-2.74 (tt, 1H, J=3.6 Hz, J=15.6 Hz) 1.92 (br, 2H), 1.70 (br, 2H); MS (ESI) m/z 378.1 (M+Na)+.

Quelle