تفاعل #91473

معادلة التفاعل

4-phenylpiperidine

EDCI

HOBt

NMM

3,4,5-trimethoxybenzoic acid

→

compound 1g

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

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   غسيلsequentially washed with water
2. 2
   تجفيفNaHCO3, brine and dried over MgSO4
3. 3
   أخرىThe solvent was removed under reduced pressure
4. 4
   أخرىto yield a crude product, which
5. 5
   أخرىwas purified by column chromatography

الإجراء التجريبي

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)+.

المصدر