Sodium Carbonate → HCID 22024220, compound

HRID 1792753Notes

Reaction equation

HRID 1792753 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].Cl[C:9]1[CH:14]=[CH:13][N:12]=[N:11][C:10]=1[Cl:15].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[Cl:15][C:10]1[N:11]=[N:12][C:13]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7])=[CH:14][CH:9]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 756345-Aminopentan-1-olHCID 2521503,4-dichloropyridazine

Product 1

HCID 22024220HCID 22024220, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-amino-1-pentanol (433 mg, 4.2 mmol), dichloropyridazine (1.25 g, 8.39 mmol) and sodium carbonate (890 mg, 8.39 mmol) was stirred in 1,4-dioxane (40 ml) and heated at 70-80° for 3 days under an atmosphere of argon. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane (300 ml) and water (38 ml). The organic layer was separated, dried and concentrated to give an orange solid which was chromatographed on silica, using hexane/ethyl acetate (1:1). The product, 5-(6chloro-3-pyridazinyl)amino-1-pentanol was isolated as a pale yellow solid (202 mg, 22%).

Workup

  1. temperatureheated at 70-80° for 3 days under an atmosphere of argon
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between dichloromethane (300 ml) and water (38 ml)
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customto give an orange solid which
  8. customwas chromatographed on silica

Sources & evidence

ORD record
ord-7b93615a1aee4f05861c3a6bb484f95d
Source dataset
uspto-grants-2006_07
Patent number
US07078403B1

Reaction notes

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