Piperidin-4-ol → 6-(4-hydroxypiperidin-1-yl)-2-methylpyridazin-3(2H)-one

HRID 919209

Reaction equation

HRID 919209 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1>CCN(C(C)C)C(C)C.O>[OH:16][CH:13]1[CH2:14][CH2:15][N:10]([C:2]2[CH:3]=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[N:7]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 79341Piperidin-4-olHCID 27836076-Chloro-2-methyl-2,3-dihydropyridazin-3-one

Product 1

HCID 867219946-(4-hydroxypiperidin-1-yl)-2-methylpyridazin-3(2H)-oneYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
120 °C

Procedure

To a slurry of 6-chloro-2-methylpyridazin-3(2H)-one (1 g, 6.94 mmol) in DIPEA (20 mL) was added piperidin-4-ol (0.84 g, 8.33 mmol) and the reaction mixture was stirred at 120° C. overnight. The resulting mixture was diluted with water (30 mL) and extracted with DCM (3×30 mL) to remove impurities. The aqueous phase was concentrated to dryness to afford the title compound as a yellow solid (1.2 g, 83%). [LCMS: Rt=1.07 min, m/z 210.1 (M+H)+].

Workup

  1. extractionextracted with DCM (3×30 mL)
  2. customto remove impurities
  3. concentrationThe aqueous phase was concentrated to dryness

Sources & evidence

ORD record
ord-521c363cd6c846688c95a399f82a0852
Source dataset
uspto-grants-2016_03
Patent number
US09273026B2

Linked notes

Loading…