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

HRID 2383362Notes

Reaction equation

HRID 2383362 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH:19]=[N:18][C:17]([C@:20]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)([OH:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC>C(Cl)Cl>[CH:28]1([C@@:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:17]2[N:18]=[CH:19][N:15]([CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:16]=2)[OH:27])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 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 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperidine-1-carboxylate (Preparation 3, 5.60 g, 12.3 mmol) was dissolved in DCM (31 ml) and 2M HCl in ether (31 ml, 60 mmol) added. After stirring at room temperature for 5 hours the solvent was removed in vacuo, and the residue partitioned between dichloromethane (200 ml) and saturated aqueous sodium bicarbonate solution (200 ml). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo to furnish the title compound as a white foam, in 92% yield, 4.03 g (contains 10% of other triazole regio-isomer).

Workup

  1. customwas removed in vacuo
  2. customthe residue partitioned between dichloromethane (200 ml) and saturated aqueous sodium bicarbonate solution (200 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-5fdc604b5ac4461db201ea796be34707
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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