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

HRID 1971875노트

반응식

HRID 1971875 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7f47e3a0ff424c818da3da4a0d9273cf
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431575B2

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