Hydrochloric Acid → 1-(6-Chloropyridazin-3-yl)piperidin-4-amine

HRID 2239568Notes

Reaction equation

HRID 2239568 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl.O1CCOCC1>C1COCC1.CO>[Cl:20][C:17]1[N:16]=[N:15][C:14]([N:11]2[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 379672514-(Boc-amino)-1-(6-chloro-3-pyridazinyl)piperidine

Product 1

HCID 64164231-(6-Chloropyridazin-3-yl)piperidin-4-amineYield 121.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

[1-(6-Chloro-pyridazin-3-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.59 g 1.89 mmol) was dissolved in THF:MeOH 2:1 (45 ml) and HCl in 1,4-dioxan (4M, 3.8 ml, 7.56 mmol) was added. The reaction was stirred at rt for 3 h and then at 60° C. for 2 h. The solvent was evaporated to yield the title compound (0.49 g, 100%) as the hydrochloric salt. 1H-NMR (CD3OD, 500 MHz): δ 8.10 (d, 1H), 7.92 (d, 1H), 4.41-4.35 (m 2H), 3.67-3.57 (m, 1H), 3.55-3.46 (m, 2H), 2.32-2.24 (m, 2H), 1.96-1.83 (m, 2H).

Workup

  1. waitat 60° C. for 2 h
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-18d61f477ddd42f49d0809730dccf846
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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