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

HRID 1270456Notes

Reaction equation

HRID 1270456 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

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-c4418328a60f4673aba7813a4b275abf
Source dataset
uspto-grants-2007_04
Patent number
US07202263B2

Reaction notes

Loading…