Hydrochloric Acid → 1-(Pyridazin-3-yl)piperidin-4-amine

HRID 2239572

Reaction equation

HRID 2239572 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:12][CH2:11][CH:10]([NH:13]C(=O)OC(C)(C)C)[CH2:9][CH2:8]2)[N:2]=1.Cl.O1CCOCC1>C1COCC1.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)[N:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86625871tert-Butyl (1-pyridazin-3-ylpiperidin-4-yl)carbamate

Product 1

HCID 624820041-(Pyridazin-3-yl)piperidin-4-amineYield 152.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

tert-Butyl (1-pyridazin-3-ylpiperidin-4-yl)carbamate (0.22 g, 0.92 mmol) was dissolved in THF:MeOH 70:30 (15 ml) and HCl in 1,4-dioxane (4M, 1.84 ml, 7.36 mmol) was added and the mixture was refluxed for 1.5 h. The reaction mixture was evaporated to yield the title compound (0.250 g, 100%) as the dihydrochloric salt. (0.250 g, 100%). 1H NMR (CD3OD, 500 MHz): δ 8.72-8.67 (m, 1H), 8.14-8.07 (m, 1H), 8.03-7.97 (m, 1H), 4.55-4.45 (m, 2H), 3.62-3.51 (m, 1H), 3.38-3.27 (m, 2H), 2.27-2.18 (m, 2H), 1.82-1.70 (m, 2H)

Workup

  1. temperaturethe mixture was refluxed for 1.5 h
  2. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-a8979ceaa767403e89bb24fc08ba9e2d
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Linked notes

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