Piperidin-4-ol → 6-(4-Hydroxypiperidin-1-yl)pyridazin-3-ol

HRID 574168

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 6-chloropyridazin-3(2H)-one (2.6 g, 20 mmol) in DIPEA (30 mL) was added piperidin-4-ol (2.4 g, 20 mmol) and the mixture was stirred at 120° C. for 8 h. The reaction mixture was concentrated under reduced pressure to afford the crude product, which was further purified by silica gel chromatography (DCM/MeOH=20/1) to afford the title compound (3.9 g, 100%) as a yellow solid. [LCMS: Rt=0.77 min, m/z 196.2 (M+H)+].

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto afford the crude product, which
customwas further purified by silica gel chromatography (DCM/MeOH=20/1)

Sources & evidence

ORD record: ord-fb9277390329402a9e2c05780f2766ab
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034874B2

Linked notes

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