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Sodium hydride → 3-[(6-(Imidazol-1-yl)pyridazin-3-yl)oxy]-1-benzylpiperidine

HRID 1609810
Notes
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Reaction equation

HRID 1609810 reaction equation
[H-].[Na+].Cl.[CH2:4]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([OH:17])[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl[C:19]1[N:20]=[N:21][C:22]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)=[CH:23][CH:24]=1>CN(C=O)C>[N:25]1([C:22]2[N:21]=[N:20][C:19]([O:17][CH:13]3[CH2:14][CH2:15][CH2:16][N:11]([CH2:4][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH2:12]3)=[CH:24][CH:23]=2)[CH:29]=[CH:28][N:27]=[CH:26]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27709033-Chloro-6-(1H-imidazol-1-yl)pyridazineHCID 162183061-Benzyl-3-piperidinol hydrochloride

Product 1

HCID 222600643-[(6-(Imidazol-1-yl)pyridazin-3-yl)oxy]-1-benzylpiperidineYield 36.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of NaH (0.21 g, 8.31 mmol) in DMF (5 mL) was added 1-benzyl-3-hydroxypiperidine hydrochloride (0.78 g, 3.3 mmol) in DMF (5 mL), and the resulting reaction mixture was stirred at ambient temperature for 30 minutes. 3-chloro-6-(imidazol-1-yl)pyridazine (0.6 g, 3.3 mmol) in DMF (5 mL) was then added dropwise. The reaction mixture was stirred at ambient temperature for 30 minutes. After removal of DMF in vacuo, the black oil was dissolved in CH2Cl2 (50 mL), washed with water and brine. Purification using column chromatography afforded 3-[(6-(imidazol-1-yl)pyridazin-3-yl)oxy]-1-benzylpiperidine (400 mg) as a yellow oil.

Workup

  1. customthe resulting reaction mixture
  2. stirringThe reaction mixture was stirred at ambient temperature for 30 minutes
  3. customAfter removal of DMF in vacuo
  4. dissolutionthe black oil was dissolved in CH2Cl2 (50 mL)
  5. washwashed with water and brine
  6. customPurification

Sources & evidence

ORD record
ord-b96741ec8f0b499787ca3a2ad84a2a5c
Source dataset
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06982259B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes