Formaldehyde → 4-(4-Benzyloxy-phenyl)-3-butyl-6-(1-methyl-piperidin-4-ylmethoxy)-pyridazine

HRID 401869Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401869
Cl.Cl.[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[C:21]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[N:20]=[N:19][C:18]=2[CH2:31][CH2:32][CH2:33][CH3:34])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C=O.[C:37](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[C:21]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28]([CH3:37])[CH2:27][CH2:26]3)[N:20]=[N:19][C:18]=2[CH2:31][CH2:32][CH2:33][CH3:34])=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 673740144-(4-Benzyloxy-phenyl)-3-butyl-6-(piperidin-4-ylmethoxy)-pyridazine dihydrochloride

Produkt 1

HCID 533718094-(4-Benzyloxy-phenyl)-3-butyl-6-(1-methyl-piperidin-4-ylmethoxy)-pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of 4-(4-benzyloxy-phenyl)-3-butyl-6-(piperidin-4-ylmethoxy)-pyridazine dihydro chloride (0.37 mmol, 190 mg) and paraformaldehyde (6.7 mmol, 611 mg) in DCM was stirred for 20 min then sodium triacetoxyborohydride (6.7 mmol, 1.41 g) was added. Stirring was continued overnight. Solvent was evaporated, and to the residue was added saturated NaHCO3. The mixture was extracted with ethyl acetate. The organic layer was washed with water, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant product was purified by column chromatography using 5% methanolic solution of ammonia (2.0 M ammonia in methanol) in DCM to provide 4-(4-benzyloxy-phenyl)-3-butyl-6-(1-methyl-piperidin-4-ylmethoxy)-pyridazine.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued overnight
  3. customSolvent was evaporated
  4. additionto the residue was added saturated NaHCO3
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe resultant product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c9b9fc2018194007b9512c529949b2ec
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741900B2

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