Sodium Carbonate → 2-(1-(6-Methylpyridazin-3-YL)piperidin-4-YL)ethanol

HRID 1195664Notes

Reaction equation

HRID 1195664 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][OH:17])[CH2:11][CH2:10]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[CH3:8][C:5]1[N:4]=[N:3][C:2]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][OH:17])[CH2:11][CH2:10]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 739534-PiperidineethanolHCID 2272543-Chloro-6-methylpyridazine

Product 1

HCID 149892172-(1-(6-Methylpyridazin-3-YL)piperidin-4-YL)ethanolYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 19.3 parts of 3-chloro-6-methylpyridazine, 19.4 parts of 4-piperidinethanol, 16 parts of sodium carbonate and 0.85 parts of N,N-dimethylacetamide was stirred for 5 hours at 150° C. After cooling, the reaction mixture was diluted with water and extracted with dichloromethane (2×). The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel;CHCl3 /CH3OH 98:2). The eluent of the desired fraction was evaporated, yielding 23.6 parts (71.1%) of 1-(6-methyl-3-pyridazinyl)-4-piperidineethanol; p. 99°-100° C. at 8 Pa (interm. 24).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane (2×)
  3. washThe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel;CHCl3 /CH3OH 98:2)
  8. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-418c3a7971b64c66a49ebf2175786139
Source dataset
uspto-grants-1992_05
Patent number
US05112825

Reaction notes

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