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Sodium Hydroxide → 1-Diphenylmethyl-4-(4'-methylbiphenyl-3-carbonyl)piperazine

HRID 22248
Notes
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Reaction equation

HRID 22248 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[C:21]1([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>C(Cl)Cl.CN(C)C=O>[C:34]1([CH:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:28]2[CH2:29][CH2:30][N:31]([C:14]([C:10]3[CH:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=4)[CH:13]=[CH:12][CH:11]=3)=[O:16])[CH2:32][CH2:33]2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 70048BenzhydrylpiperazineHCID 27739784'-Methyl-biphenyl-3-carboxylic acid

Product 1

HCID 194302781-Diphenylmethyl-4-(4'-methylbiphenyl-3-carbonyl)piperazineYield 82.1%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 4'-methylbiphenyl-3-carboxylic acid (2.2 g) in a mixture of methylene chloride (20 ml) and dimethylformamide (0.5 ml) was added thionyl chloride (1.48 g). The mixture was refluxed until the suspension dissolved, after which the temperature was allowed to cool to room temperature. To this solution was added 1-(diphenylmethyl)piperazine (3.94 g) in methylene chloride dropwise, and the reaction mixture allowed to stand overnight. Sodium hydroxide (30 ml of 1N) and 50 ml of methylene chloride was added, the organic layer separated, washed with brine, dried over sodium sulfate, and solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with 25% ethyl acetate in heptane, to yield 3.8 g of 1-diphenylmethyl-4-(4'-methylbiphenyl-3-carbonyl)piperazine. The dihydrochloride salt was prepared and recrystallized from ethanol, m.p. 226° C.

Workup

  1. temperatureThe mixture was refluxed until the suspension
  2. dissolutiondissolved
  3. customthe organic layer separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate, and solvent
  6. customremoved under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 25% ethyl acetate in heptane

Sources & evidence

ORD record
ord-e481b8e584144ef89b2fb87ecd0fa678
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05428037

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes