1-Acetylpiperazine → 1-Acetyl-4-(4-fluorophenylcarbonylmethyl)-piperazine hydrochloride

HRID 49796

Reaction equation

HRID 49796 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:13].C(=O)([O-])O.[K+]>C(#N)C>[ClH:10].[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 837951-AcetylpiperazineHCID 1202482-Chloro-4'-fluoroacetophenoneHCID 516893Potassium Bicarbonate

Product 1

HCID 99044421-Acetyl-4-(4-fluorophenylcarbonylmethyl)-piperazine hydrochlorideYield 99.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-acetylpiperazine (0.627 g), 2-chloro-4′-fluoroacetophenone (0.844 g), and potassium hydrogen carbonate (0.735 g) in acetonitrile (12 ml) was stirred at ambient temperature for 3 days. After removal of the solid by filtration, the filtrate was evaporated under reduced pressure to give a residue, which was chromatographed on silica gel (100 ml) eluting with 0%-5% methanol in dichloromethane. The objective compound of the free form was taken up into ethyl acetate (2 ml) and to the solution was added a solution of hydrogen chloride in ethyl acetate (4N, 2 ml). The resulting precipitate was collected by filtration, washed with diisopropyl ether, and dried in vacuo to give 1-acetyl-4-(4-fluorophenylcarbonylmethyl)-piperazine hydrochloride (1.47 g).

Workup

  1. customAfter removal of the solid
  2. filtrationby filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customto give a residue, which
  5. customwas chromatographed on silica gel (100 ml)
  6. washeluting with 0%-5% methanol in dichloromethane
  7. additionwas added a solution of hydrogen chloride in ethyl acetate (4N, 2 ml)
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with diisopropyl ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-3e6c4ebfd1b54107b7d522df8874cc92
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Linked notes

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