Formaldehyde → HCID 22037512, compound

HRID 1167567Notes

Reaction equation

HRID 1167567 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:4][CH2:3]1.[CH2:26]=O>C(O)=O>[CH3:26][N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 22037252HCID 22037252, compound

Product 1

HCID 22037512HCID 22037512, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 5-(4-piperidyl)-4-(4-pyridyl)-3-(4-chlorophenyl)pyrazole hydrochloride (Example C-74) (25 g, 61 mmol) in 140 mL of formic acid (96%) was added 50 g of formaldehyde (37%). The solution was stirred at 75° C. for 48 h and was cooled to room temperature. The excess formic acid was removed under reduced pressure and the residue was dissolved in 100 mL of water. The solution was added to concentrated NH4OH/H2O and the mixture was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine (1×250 mL) and was dried over Na2SO4. The solution was filtered and concentrated to leave a white solid. The solid was triturated with ether and was filtered to afford the title compound: MS (M+H): 353 (base peak).

Workup

  1. temperaturewas cooled to room temperature
  2. customThe excess formic acid was removed under reduced pressure
  3. dissolutionthe residue was dissolved in 100 mL of water
  4. additionThe solution was added to concentrated NH4OH/H2O
  5. extractionthe mixture was extracted with ethyl acetate (3×200 mL)
  6. washThe combined organic layers were washed with brine (1×250 mL)
  7. dry with materialwas dried over Na2SO4
  8. filtrationThe solution was filtered
  9. concentrationconcentrated
  10. customto leave a white solid
  11. customThe solid was triturated with ether
  12. filtrationwas filtered

Sources & evidence

ORD record
ord-954c5e30affb4a5cae2d108c1af7db99
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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