Methanol → HCID 14989222, compound

HRID 981637Notes

Reaction equation

HRID 981637 reaction equation
[Na].Cl[C:3]1[N:8]=[N:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][OH:17])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:18][OH:19]>>[CH3:18][O:19][C:3]1[N:8]=[N:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][OH:17])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 149892211-(6-Chloro-3-pyridazinyl)-4-piperidineethanol

Product 1

HCID 14989222HCID 14989222, compoundYield 61.5%

Procedure

5.7 Parts of sodium (in pieces) were added to 86 parts of methanol. After the dropwise addition of 12.1 parts of 1-(6-chloro-3-pyridazinyl)-4-piperidineethanol, the reaction mixture was stirred overnight at reflux temperature. After cooling, the whole was poured into ice water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of methylbenzene and methanol (90:10 by volume) as eluent. The desired fraction was collected and the eluent was evaporated, yielding 7.3 parts (61.5%) of 1-(6-methoxy-3-pyridazinyl)-4-piperidineethanol as a residue (int. 95).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. extractionthe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of methylbenzene and methanol (90:10 by volume) as eluent
  9. customThe desired fraction was collected
  10. customthe eluent was evaporated

Sources & evidence

ORD record
ord-052d8533d4724ed88b8cfd26b9e3730d
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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