Water → HCID 22037958, compound

HRID 1790436Notes

Reaction equation

HRID 1790436 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([Br:23])[CH:21]=4)C=C3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O>O1CCCC1.FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:22]3[CH:17]=[CH:18][CH:19]=[C:20]([Br:23])[CH:21]=3)[CH2:10][CH2:9]2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 962WaterHCID 220381881-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-bromoindole

Product 1

HCID 22037958HCID 22037958, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling, a 1 M solution (20 ml) of a borane/tetrahydrofuran complex in tetrahydrofuran was added dropwise into a solution of 1-[1-(4-fluorophenethyl)-piperidin-4-yl]-6-bromoindole (3.9 g) in trifluoroacetic acid (50 ml) followed by stirring for 3 hr. After adding water thereto and concentrating under reduced pressure, the reaction mixture was basified by adding ethanol and a 5 N aqueous solution of sodium hydroxide and then stirred for 30 min. Next, a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added thereto and the layers were separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The residue was then purified by silica gel column chromatography (toluene/acetone system) to give the title compound (2.0 g) as a white powder (yield: 51%).

Workup

  1. concentrationconcentrating under reduced pressure
  2. additionby adding ethanol
  3. stirringa 5 N aqueous solution of sodium hydroxide and then stirred for 30 min
  4. additionNext, a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added
  5. customthe layers were separated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe residue was then purified by silica gel column chromatography (toluene/acetone system)

Sources & evidence

ORD record
ord-c939434da50a4458820aa9fba936657c
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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