تفاعل #1593053

معادلة التفاعل

1-bromo-4-bromomethylbenzene

cis-2,6-dimethylpiperidine

potassium carbonate

→

title compound

المردود 82.2%

1-(4-Bromobenzyl)-cis-2,6-dimethylpiperidine

المردود 82.2%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةunder reflux for 2 h
3. 3
   أخرىthe solid removed by filtration
4. 4
   أخرىthe filtrate evaporated in vacuo
5. 5
   أخرىThe resultant residue was partitioned between ethyl acetate (100 mL) and water (25 mL)
6. 6
   تجفيفThe organic phase was dried over anhydrous sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated in vacuo

الإجراء التجريبي

A mixture of 1-bromo-4-bromomethylbenzene (500 mg, 2.0 mmol), cis-2,6-dimethylpiperidine (0.30 mL, 2.2 mmol) and potassium carbonate (332 mg, 2.4 mmol) in acetonitrile (20 mL) was heated under reflux for 2 h. The reaction mixture was allowed to cool to ambient temperature, the solid removed by filtration and the filtrate evaporated in vacuo. The resultant residue was partitioned between ethyl acetate (100 mL) and water (25 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to give the title compound as a pale brown oil (464 mg, 82%). 1H NMR (CDCl3, 300 MHz): 7.40 (d, J=8.3 Hz, 2H), 7.27 (d, J=7.0 Hz, 2H), 3.71 (s, 2H), 2.56-2.36 (m, 2H), 1.68-1.61 (m, 1H), 1.61-1.47 (m, 2H), 1.33-1.24 (m, 3H), 1.01 (d, J=6.2 Hz, 6H). LCMS (Method B): RT=0.8 min, M+H+=282/284.

المصدر