Water → 1-Benzyl-1,2,3,4-tetrahydroquinolin-7-ol

HRID 131174Notes

Reaction equation

HRID 131174 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:13]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 939807-Quinolinol, 1,2,3,4-tetrahydro-

Product 1

HCID 218649361-Benzyl-1,2,3,4-tetrahydroquinolin-7-olYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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=5.0Hz, 2H), 2.73 (t, J=5.8Hz, 2H) 1.98 (m, 2H); MS LC-MS (MH+=240.1), LC MS RT: 3.08 min.

Workup

  1. extractionextracted it with methylene chloride several times
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltrated
  4. customThe solution was evaporated under vacuum
  5. customThe crude residue was purified by MPLC (biotage)

Sources & evidence

ORD record
ord-6f843fb05eca4917b96a7c870f649b22
Source dataset
uspto-grants-2008_06
Patent number
US07384947B2

Reaction notes

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