N-methyl-2-pyrrolidone → (5'-Benzyl-3',4'-dimethyl-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-yl)-methanol

HRID 447103Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[CH2:9]([C:16]1N=[N:18][C:19](Cl)=[C:20]([CH3:23])[C:21]=1[CH3:22])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:25]N1C(=O)CCC1>C(Cl)Cl>[CH2:9]([C:16]1[C:21]([CH3:22])=[C:20]([CH3:23])[C:19]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]2)=[N:18][CH:25]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 210 °C

Procedure

To the solution of piperidin-4-yl-methanol (125 mg, 1.03 mmol) in NMP (3 mL) is added 3-benzyl-6-chloro-4,5-dimethyl-pyridazine (60 mg, 0.258 mmol) and TEA. The reaction mixture is stirred at 210° C. in a microwave reactor for 2 h. Then the reaction mixture is diluted with DCM (15 mL) and washed with NaHCO3 and water. The organic solvent is separated and removed under reduced pressure. Purification by HPLC of the crude product with acetonitrile in water (from 20% to 100% with 3% 1-propanol) at 220 nm wavelength detection provides the desired product as off white powder (200 mg, 62%).

Workup

washwashed with NaHCO3 and water
customThe organic solvent is separated
customremoved under reduced pressure
customPurification by HPLC of the crude product with acetonitrile in water (from 20% to 100% with 3% 1-propanol) at 220 nm wavelength detection

Sources & evidence

ORD record: ord-d87dc9bc7dba409992cb6dad57e65764
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481542B2

Reaction notes

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