Piperidine → HCID 21451309, compound

HRID 596276Notes

Reaction equation

HRID 596276 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5](Cl)=[C:4]2[CH:9]=[N:10][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:12]([CH2:13][CH3:14])[C:3]=12.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH2:13]([C:12]1[C:3]2[C:4](=[C:5]([N:10]3[CH2:11][CH2:12][CH2:3][CH2:4][CH2:9]3)[N:6]=[N:7][C:2]=2[N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:9]=[N:10][C:11]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14]

Participants

3

Reactant 2

HCID 8082PiperidineHCID 12324664HCID 12324664, compound

Product 1

HCID 21451309HCID 21451309, compound

Procedure

3.0 g. of 1,4-dichloro-8-ethyl-7-phenylpyrido[3,4-d]-pyridazine was heated together with 15 g. of piperidine at 120° C for 1.5 hours, after which time the excess piperidine was distilled off. To the residue was added 60 ml. of water and the resultant crystals were recovered by filtration and were chromatographed on a column packed with silica gel, followed by elution with a mixed solvent of acetone-benzene (1:8). The combined eluate is concentrated and the residue was dissolved in 100 ml. of ethanol. Following the addition of 5 ml. of water, the solution was concentrated to dryness. The concentrate was diluted with 100 ml. of water and stirred, whereupon 2.5 g. of 8-ethyl-7-phenyl-1,4-dipiperidinopyrido-[3,4-d]pyridazine was obtained. Melting point: 64°-65° C.

Workup

  1. distillationafter which time the excess piperidine was distilled off
  2. additionTo the residue was added 60 ml
  3. filtrationof water and the resultant crystals were recovered by filtration
  4. customwere chromatographed on a column
  5. washfollowed by elution with a mixed solvent of acetone-benzene (1:8)
  6. concentrationThe combined eluate is concentrated
  7. dissolutionthe residue was dissolved in 100 ml
  8. additionthe addition of 5 ml
  9. concentrationof water, the solution was concentrated to dryness
  10. additionThe concentrate was diluted with 100 ml

Sources & evidence

ORD record
ord-a56c6a0ed4124e0d9d7667d4413ff9d8
Source dataset
uspto-grants-1977_03
Patent number
US04010265

Reaction notes

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