Hydrochloric Acid → 3-Butyl-4-(4-cyclohexyloxy-phenyl)-6-(4-fluoro-piperidin-4-ylmethoxy)-pyridazine dihydrochloride

HRID 2168684Notes

Reaction equation

HRID 2168684 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][O:16][C:17]2[N:18]=[N:19][C:20]([CH2:36][CH2:37][CH2:38][CH3:39])=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:25][CH:24]=3)[CH:22]=2)([F:14])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:40]>C(Cl)Cl.O1CCOCC1>[ClH:40].[ClH:40].[CH2:36]([C:20]1[N:19]=[N:18][C:17]([O:16][CH2:15][C:11]2([F:14])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:22][C:21]=1[C:23]1[CH:24]=[CH:25][C:26]([O:29][CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)=[CH:27][CH:28]=1)[CH2:37][CH2:38][CH3:39]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 673744624-[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxymethyl]-4-fluoro-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 673713573-Butyl-4-(4-cyclohexyloxy-phenyl)-6-(4-fluoro-piperidin-4-ylmethoxy)-pyridazine dihydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxymethyl]-4-fluoro-piperidine-1-carboxylic acid tert-butyl ester (0.15 mmol, 85 mg) in DCM (1 mL) was added 4 N HCl in dioxane (1.5 mL) and the reaction was stirred for 30 min. The volatiles were removed in vacuo and the residue was triturated with anhydrous ethyl ether (2×3 mL) and dried under high vacuum to provide 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(4-fluoro-piperidin-4-ylmethoxy)-pyridazine dihydrochloride (0.078 g).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was triturated with anhydrous ethyl ether (2×3 mL)
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-9ba96801f19449b99aacf6821d0738d3
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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