Hydrazine → N-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-4-N,1-dimethyl-4-piperidinamine, dihydrate

HRID 489966Notes

Reaction equation

HRID 489966 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[C:9](=[C:16]2SCS2)[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][CH:25]([NH:28][CH3:29])[CH2:24][CH2:23]1.[NH2:30][NH2:31]>C1(C)C=CC=CC=1>[OH2:20].[OH2:20].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:31][N:30]=[C:16]([N:28]([CH3:29])[CH:25]3[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]3)[C:9]=2[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 5663231-Methyl-4-(methylamino)piperidineHCID 155168911-(4-Chlorophenyl)-2-(1,3-dithietan-2-ylidene)-2-(4-pyridinyl)ethanone

Product 1

HCID 131723417N-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-4-N,1-dimethyl-4-piperidinamine, dihydrate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(4-chlorophenyl)-2-(1,3-dithietan-2-ylidene)-2-(4-pyridinyl)ethanone (3.2 g, 0.01 mol; prepared as set forth in Step 1 of Example A-341) and 1-methyl-4-methylaminopiperidine (3.8 g, 0.03 mol) in 30 mL of toluene refluxed for six hours under nitrogen; The mixture was cooled and solvent was removed under vacuum. The residue was dissolved in dry tetrahydrofuran (30 mL) and anyhydrous hydrazine (650 mg, 0.02 mol) was added. The reaction mixture was stirred at room temperature under nitrogen for 16 hours. The resulting precipitate was filtered and warmed in methanol and a few drops of concentrated ammonium hydroxide. The mixture was filtered hot and the filtrate blown down to half the volume. As the filtrate cooled, a product separated and was filtered to give 395 of pure N-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-4-N,l-dimethyl-4-piperidinamine, dihydrate, m.p. 260-261° C. Anal. Calc'd for C21H24ClN5.2H2O: C, 60.35; H, 6.75; N, 16.76. Found: C, 59.89; H, 6.56; N: 16.40.

Workup

  1. customprepared
  2. temperaturerefluxed for six hours under nitrogen
  3. temperatureThe mixture was cooled
  4. customsolvent was removed under vacuum
  5. dissolutionThe residue was dissolved in dry tetrahydrofuran (30 mL)
  6. filtrationThe resulting precipitate was filtered
  7. temperaturewarmed in methanol
  8. filtrationThe mixture was filtered hot
  9. temperatureAs the filtrate cooled
  10. customa product separated
  11. filtrationwas filtered

Sources & evidence

ORD record
ord-59b4e1534191417ab728b75939df016b
Source dataset
uspto-grants-2005_12
Patent number
US06979686B1

Reaction notes

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