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

HRID 447103
Notes
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Reaction equation

HRID 447103 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 4207714-PiperidinemethanolHCID 591914873-Benzyl-6-chloro-4,5-dimethylpyridazine

Product 1

HCID 68550385(5'-Benzyl-3',4'-dimethyl-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-yl)-methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. washwashed with NaHCO3 and water
  2. customThe organic solvent is separated
  3. customremoved under reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes