Triethylamine → HCID 58547327, compound

HRID 1850272Notes

Reaction equation

HRID 1850272 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1Cl.[NH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1.CCN(CC)CC>CS(C)=O.O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 951233,4,6-TrichloropyridazineHCID 4207714-Piperidinemethanol

Product 1

HCID 58547327HCID 58547327, compoundYield 75.99%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3,4,6-trichloro-pyridazine (59) (364 mg, 2 mmol) and piperidin-4-yl-methanol (35) (253 mg, 2.2 mmol) in DMSO (5 mL) was added Et3N (404 mg, 4 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (30 mL×3). The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel to give [1-(3,6-dichloro-pyridazin-4-yl)-piperidin-4-yl]-methanol (60) (292.3 mg, 1.12 mmol, yield 75.99%).

Workup

  1. extractionextracted with EtOAc (30 mL×3)
  2. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-115acc158be94e478cbb9aed5edcd101
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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