Formaldehyde → HCID 15541506, compound

HRID 489963Notes

Reaction equation

HRID 489963 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:9]=2[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.[CH2:25]=O>C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH3:25])[CH2:15][CH2:14]3)[C:9]=2[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 22037186HCID 22037186, compound

Product 1

HCID 15541506HCID 15541506, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
60 °C

Procedure

The compound of Example A-170 was also synthesized in the following manner. 1-[5-(4-Chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]piperazine (12.2 g, 36 mmol, prepared as set forth in Example A-169), 88% formic acid (20 mL), and formaldehyde (37% formalin solution; 44 g, 540 mmol) were combined and stirred at 60° C. for 16 hours under a nitrogen atmosphere. Excess solvent was removed on the rotary evaporator and the residue was dissolved in water (150 mL). The pH was adjusted to 8-9 by addition of solid sodium bicarbonate. The resulting precipitate was filtered and air dried. It was then treated with hot methanol (400 mL), filtered and blown down to a volume of 75 mL, cooled and filtered. After drying in a vacuum is oven at 80° C. overnight, there was obtained 8.75 g (68%) of 1-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-4-methylpiperazine, m.p. 262-264° C. Anal. Calc'd. for C19H20N5Cl: C, 64.49; H, 5.70; N, 19.79. Found: C, 64.04; H, 5.68; N, 19.63.

Workup

  1. customExcess solvent was removed on the rotary evaporator
  2. dissolutionthe residue was dissolved in water (150 mL)
  3. additionThe pH was adjusted to 8-9 by addition of solid sodium bicarbonate
  4. filtrationThe resulting precipitate was filtered
  5. customair dried
  6. additionIt was then treated with hot methanol (400 mL)
  7. filtrationfiltered
  8. temperaturecooled
  9. filtrationfiltered
  10. customAfter drying in a vacuum
  11. customat 80° C.
  12. customovernight

Sources & evidence

ORD record
ord-a5d7569c38364e3e868204bfc0e31ff5
Source dataset
uspto-grants-2005_12
Patent number
US06979686B1

Reaction notes

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