Hydrochloric Acid → HCID 86657801, compound

HRID 1971957Notes

Reaction equation

HRID 1971957 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([OH:14])[C@H:10]([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)[CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[CH2:36]([C:20]1[N:19]=[N:18][C:17]([O:16][CH2:15][C@H:10]2[C@@H:11]([OH:14])[CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:22][C:21]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=1)[CH2:37][CH2:38][CH3:39]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86657800HCID 86657800, compound

Product 1

HCID 86657801HCID 86657801, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (±)-cis-3-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxymethyl]-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.37 mmol, 0.2 g) in DCM (2 mL) was added 4 N HCl in dioxane (4 mL) and continued stirring for 1 h at room temperature. The volatiles were removed under reduced pressure; residue was dissolved in DCM, added hexanes to precipitate the desired HCl salt. Solvent was removed under reduced pressure and the solid was dried under high vacuum to provide (±)-cis-3-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxymethyl]-piperidin-4-ol.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionresidue was dissolved in DCM
  3. additionadded hexanes
  4. customto precipitate the desired HCl salt
  5. customSolvent was removed under reduced pressure
  6. customthe solid was dried under high vacuum

Sources & evidence

ORD record
ord-2f43dbd82af94781ac3ca41cc86d8657
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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