تفاعل #944140

معادلة التفاعل

water

1,2,3,4-tetrahydro-quinolin-7-ol

bromomethyl-benzene

potassium carbonate

→

title compound

المردود 93.0%

1-benzyl-1,2,3,4-tetrahydro-quinolin-7-ol

المردود 93.0%

المذيبات

N,N-dimethyl-formamide

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted it with methylene chloride several times
2. 2
   تجفيفdried over magnesium sulfate
3. 3
   ترشيحfiltrated
4. 4
   أخرىThe solution was evaporated under vacuum
5. 5
   أخرىThe crude residue was purified by MPLC (biotage)

الإجراء التجريبي

To a solution of 1,2,3,4-tetrahydro-quinolin-7-ol (200 mg, 1.34 mmol) from step 1 in anhydrous N,N-dimethyl-formamide (5 mL) was added bromomethyl-benzene (229 mg, 1.34 mmol), and potassium carbonate (556 mg, 4.02 mmol). The reaction mixture was stirred at 60° C. overnight. Added some water to the reaction mixture and extracted it with methylene chloride several times. The organic layer was combined, dried over magnesium sulfate, and filtrated. The solution was evaporated under vacuum. The crude residue was purified by MPLC (biotage) to afford 297 mg (93%) of the title compound. 1H-NMR (CDCl3) δ 7.35–7.20 (m, 5H), 6.81 (d, J=8.1 Hz, 1H), 6.05 (dd, J=7.8 Hz, 2.2 Hz, 1H), 5.98 (d, 2.5 Hz, 1H), 4.53 (bs, 1H), 4.44 (s, 2H), 3.34 (t, J=5.0 Hz, 2H), 2.73 (t, J=5.8 Hz, 2H), 1.98 (m, 2H); MS LC-MS (MH+=240.1), LC MS RT: 3.08 min.

المصدر