4-Fluorobenzoyl chloride → Benzamide, N-(1-acetyl-4-piperidinyl)-4-fluoro-

HRID 49780Notes

Reaction equation

HRID 49780 reaction equation
Cl.[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1)(=[O:4])[CH3:3].C(N(C(C)C)CC)(C)C.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>ClCCl>[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([F:21])=[CH:23][CH:24]=2)[CH2:7][CH2:6]1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 172216421-Acetyl-4-aminopiperidine hydrochloride

Product 1

HCID 9816738Benzamide, N-(1-acetyl-4-piperidinyl)-4-fluoro-Yield 53,342.699%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 1-acetyl-4-aminopiperidine hydrochloride (715 mg) in dichloromethane (7 ml) were added diisopropylethylamine (1.83 ml) and a solution of 4-fluorobenzoyl chloride (0.83 mg) in dichloromethane (2 ml) at ambient temperature. After stirring for 6.5 hours, the reaction mixture was diluted with dichloromethane and washed with water, saturated aqueous sodium hydrogen carbonate, and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. A residue was purified by column chromatography (silica gel 50 ml, dichloromethane:methanol=50:1 to 10:1). After rinse with diisopropyl ether, N-(1-acetylpiperidin-4-yl)-4-fluorobenzamide (738 mg) was obtained.

Workup

  1. customat ambient temperature
  2. washwashed with water, saturated aqueous sodium hydrogen carbonate, and brine
  3. dry with materialAfter drying with magnesium sulfate
  4. customthe solvents were removed under reduced pressure
  5. customA residue was purified by column chromatography (silica gel 50 ml, dichloromethane:methanol=50:1 to 10:1)
  6. washAfter rinse with diisopropyl ether

Sources & evidence

ORD record
ord-b1bfce6118a44d519d26676af9fb78b1
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Reaction notes

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