Hydrochloric Acid → (R)-cyclohexyl(phenyl)[1-(piperidin-4-ylmethyl)-1H-1,2,4-triazol-3-yl]methanol

HRID 2383363Notes

Reaction equation

HRID 2383363 reaction equation
[CH:1]1([C@@:7]([OH:33])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:8]2[N:12]=[CH:11][N:10]([CH2:13][CH:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCOCC1>[CH:27]1([C@@:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:8]2[N:12]=[CH:11][N:10]([CH2:13][CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:9]=2)[OH:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59145956Tert-butyl4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperidine-1-carboxylate

Product 1

HCID 59145948(R)-cyclohexyl(phenyl)[1-(piperidin-4-ylmethyl)-1H-1,2,4-triazol-3-yl]methanolYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Tert-butyl 4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperidin-1-carboxylate (Preparation 3a, 2.00 g, 4.40 mmol) was dissolved in dioxane (11 ml) and stirred vigorously to achieve solubilisation. 4M HCl in dioxane (5.54 mL, 22.1 mmol) was then added. After stirring at room temperature for 24 hours the solvent was removed in vacuo, and the residue partitioned between dichloromethane (50 mL) and saturated aqueous sodium bicarbonate solution (50 mL). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo to furnish the title compound as a colourless oil, in 96% yield, 1.5 g.

Workup

  1. stirringAfter stirring at room temperature for 24 hours the solvent
  2. customwas removed in vacuo
  3. customthe residue partitioned between dichloromethane (50 mL) and saturated aqueous sodium bicarbonate solution (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-14392182962b4ef1ba4f148f8f873269
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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