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

HRID 1167559Notes

Reaction equation

HRID 1167559 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,1-dimethyl-4-piperidinamine, dihydrate, m.p. 260-261° C. Anal. Calc'd in 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-2300b5c69c4a4f2dad31e47248745122
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

Loading…