Water → HCID 15462959, compound

HRID 397604Notes

Reaction equation

HRID 397604 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

3.13 g (31 mmol) of 4-hydroxypiperidine were dissolved in 30 ml of dimethylformamide (DMF), followed by the addition of 7.94 g (31 mmol) of α-cyclopropylcarbonyl-2-fluorobenzyl bromide 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 and the resulting mixture was extracted with toluene. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure. The resulting 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. extractionthe resulting mixture was extracted with toluene
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography on a silica gel column (eluting solvent: chloroform/methanol=19/1)

Sources & evidence

ORD record
ord-27360afc19c647c697dfdad8b5b2e0b8
Source dataset
uspto-grants-2003_08
Patent number
US06610708B1

Reaction notes

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