Sodium Carbonate → 2-[1-(3,6-Dichloropyridazin-4-yl)piperidin-4-yl]ethan-1-ol

HRID 1958080Notes

Reaction equation

HRID 1958080 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1Cl.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C(=O)C.[NH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]1>O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 739534-PiperidineethanolHCID 951233,4,6-Trichloropyridazine

Product 1

HCID 714237102-[1-(3,6-Dichloropyridazin-4-yl)piperidin-4-yl]ethan-1-olYield 43.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 mL round bottom flask, 9.18 g (0.05 mol) of 3,4,6-trichloro-pyridazine, 5.30 g (0.05 mol) of anhydrous sodium carbonate and 20 mL of N,N-dimethylacetamide (DMA) were added, stirred at room temperature, then 6.54 g (0.05 mol) of 2-(piperidin-4-yl)-ethanol (dissolved in 10 mL DMA) was added dropwise slowly, after the dropwise addition, the agitation was kept overnight, the reaction liquid was poured into 100 mL of distilled water on the next day, extracted for three times by using total 200 mL of dichloromethane, the extract solutions were combined together, dried over anhydrous Na2SO4, concentrated, and separated by using column chromatograph (eluent, petroleum ether:acetone=10:3) to obtain 6 g of 2-[1-(3,6-dichloro-pyridazin-4-yl)-piperidin-4-yl]-ethanol, yield: 43.6%, 1H-NMR(400 MHz, DMSO-D6) δppm: 1.21˜1.31(m, 2H), 1.39˜1.43(m, 2H), 1.59 ˜1.67(m, 1H), 1.76 ˜1.79(dbrs, 2H), 2.82 ˜2.88(dt, 2H, J=11 Hz), 3.45˜3.49(m, 2H), 3.70˜3.73(dbrs, 2H), 4.40˜4.42(t, 1H, J=5 Hz), 7.35(s, 1H).

Workup

  1. additionafter the dropwise addition
  2. customthe reaction liquid
  3. extractionextracted for three times
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customseparated

Sources & evidence

ORD record
ord-b8585840cf5641f389f3afdd905c4e04
Source dataset
uspto-grants-2013_04
Patent number
US08410105B2

Reaction notes

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