Methyl vinyl ketone → 1-[2-(Bis-(4-fluorophenyl)-methoxy)-ethyl]-4-(3-ketobutyl)piperazine

HRID 1197514Notes

Reaction equation

HRID 1197514 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH3:25][C:26]([CH:28]=[CH2:29])=[O:27].C(O)(=O)/C=C\C(O)=O>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:29][CH2:28][C:26](=[O:27])[CH3:25])[CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 444266Maleic AcidHCID 99740131-[2-[Bis(4-fluorophenyl)methoxy]ethyl]piperazine

Product 1

HCID 191067251-[2-(Bis-(4-fluorophenyl)-methoxy)-ethyl]-4-(3-ketobutyl)piperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.7 g (2.1 mM) of 1-[2-(bis-(4-fluorophenyl) -methoxy)-ethyl]piperazine and 150 mg (2.1 mM) of freshly distilled methylvinyl-ketone was stirred at room temperature for 2 h. 30 ml of ethanol and 0.48 g of maleic acid were added, the precipitated salt was isolated by filtration and recrystallized from hot acetonitrile to yield the dimaleate salt of the title compound as colourless crystals melting at 159°-160° C. Analytical data were in accordance with the proposed structure.

Workup

  1. customthe precipitated salt was isolated by filtration
  2. customrecrystallized from hot acetonitrile

Sources & evidence

ORD record
ord-aa1d00423dba468ebc12f1be8a6b059b
Source dataset
uspto-grants-1994_01
Patent number
US05276035

Reaction notes

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