Formaldehyde → 1-[[1,5-Bis(4-chlorophenyl)-2-methyl-pyrrol-3-yl]methyl]-4-[3-(trifluoromethyl)phenyl]piperazine

HRID 2357714Notes

Reaction equation

HRID 2357714 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.Cl.[F:22][C:23]([F:37])([F:36])[C:24]1[CH:25]=[C:26]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:27]=[CH:28][CH:29]=1.[CH2:38]=O.[OH-].[Na+]>C(#N)C.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[CH:10][C:11]([CH2:38][N:33]3[CH2:34][CH2:35][N:30]([C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:22])([F:36])[F:37])[CH:25]=4)[CH2:31][CH2:32]3)=[C:12]2[CH3:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 4569171,2-Bis(4-chlorophenyl)-5-methylpyrroleHCID 3084246TFMPP hydrochloride

Product 1

HCID 30113901-[[1,5-Bis(4-chlorophenyl)-2-methyl-pyrrol-3-yl]methyl]-4-[3-(trifluoromethyl)phenyl]piperazineYield 66.24%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1,2-bis(4-chlorophenyl)-5-methylpyrrole (1.76 g, 0.006 mol, as obtained in Step-2) in acetonitrile (18 ml) was added a mixture of 1-(3-trifluoromethylphenyl) piperazine hydrochloride (1.55 g, 0.006 mol), 40% formaldehyde (0.45 ml, 0.006 mol) and acetic acid (5.23 ml) drop-wise. After the completion of addition, the reaction mixture was stirred at room temperature for 3-4 hours. The reaction mixture was neutralized with NaOH (20% aq. soln.) and extracted with ethyl acetate (2×100 ml). The combined ethyl acetate extract was washed with water (2×50 ml), brine (1×30 ml), dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was purified by column chromatography over silica gel using ethyl acetate hexane (80:10) as eluent to give 2.1 g (66.24%) of the title compound.

Workup

  1. additionAfter the completion of addition
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water (2×50 ml), brine (1×30 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent evaporated off
  7. customThe crude product so obtained
  8. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-7b277eb62ce842de8c08beb4b5f7003e
Source dataset
uspto-grants-2010_07
Patent number
US07763602B2

Reaction notes

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