Water → HCID 15462959, compound

HRID 2288029Notes

Reaction equation

HRID 2288029 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH:8]1([C:11]([CH:13](Br)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[O:12])[CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:8]1([C:11]([CH:13]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[O:12])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 234358712-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethan-1-one

Product 1

HCID 15462959HCID 15462959, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 ml of dimethylformamide (DMF), 3.13 g (31 mmol) of 4-hydroxypiperidine were dissolved, followed by the addition of 7.94 g (31 mmol) of α-cyclopropylcarbonyl-2-fluorobenzylbromide and 4.7 g (34 mmol) of potassium carbonate. The resulting mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with toluene. The resulting organic layer was dried over anhydrous sodium sulfate. The solvent was concentrated by evaporation under reduced pressure. The residue was purified by chromatography on a silica gel column (eluting solvent: chloroform/methanol=19/1), whereby 8.00 g of the title compound were obtained as a brown oil (yield: 93%).

Workup

  1. extractionfollowed by extraction with toluene
  2. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated by evaporation under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (eluting solvent: chloroform/methanol=19/1)

Sources & evidence

ORD record
ord-eb43488317db414eb46c72cf4bb2dbbb
Source dataset
uspto-grants-2000_07
Patent number
US06087379

Reaction notes

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