2-Fluoroethyl bromide → 1-(2-Fluoroethyl)-1,2,3,4-tetrahydro-7-quinolinol

HRID 2099016Notes

Reaction equation

HRID 2099016 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][CH2:14][F:15].C(N(C(C)C)CC)(C)C>CN(C=O)C>[F:15][CH2:14][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

Participants

5

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 81531DiisopropylethylamineHCID 939807-Quinolinol, 1,2,3,4-tetrahydro-

Product 1

HCID 858634731-(2-Fluoroethyl)-1,2,3,4-tetrahydro-7-quinolinolYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg (3.35 mmol) 1,2,3,4-Tetrahydro-quinolin-7-ol are dissolved in 8 mL DMF and stirred at 60° C. overnight with 0.325 mL (1.3 eq) 1-bromo-2-fluoroethane, in the presence of 0.63 mL (1.1 eq) diisopropylethylamine. The reaction mixture is extracted with 0.1 N aqu. HCl and ethyl acetate. The combined organic extracts are washed with brine, dried over sodium acetate and evaporated. The residue is column chromatographed (silica gel, ethyl acetate/petroleum ether 1:2 to 1:1) to yield 290 mg (44%) desired product as a brown oil.

Workup

  1. extractionThe reaction mixture is extracted with 0.1 N aqu
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over sodium acetate
  4. customevaporated
  5. customchromatographed (silica gel, ethyl acetate/petroleum ether 1:2 to 1:1)

Sources & evidence

ORD record
ord-ea436ee646474ad3b1fcd5f35788c6be
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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