Formaldehyde → HCID 15541506, compound

HRID 1167556Notes

Reaction equation

HRID 1167556 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 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 oven at 80° C. overnight

Sources & evidence

ORD record
ord-2c44687c3b084dd7a23b7d4a3fa695da
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

Loading…