Hydrochloric Acid → 1-[3-(1H-1,2,3-triazol-1-yl)phenyl]piperidin-4-ol

HRID 1808744Notes

Reaction equation

HRID 1808744 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH:25]=[CH:24][N:23]=[N:22]3)[CH:16]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.Cl>C(O)C>[N:21]1([C:17]2[CH:16]=[C:15]([N:12]3[CH2:11][CH2:10][CH:9]([OH:8])[CH2:14][CH2:13]3)[CH:20]=[CH:19][CH:18]=2)[CH:25]=[CH:24][N:23]=[N:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 706645084-{[tert-butyl(dimethyl)silyl]oxy}-1-[3-(1H-1,2,3-triazol-1-yl)phenyl]piperidine

Product 1

HCID 706645131-[3-(1H-1,2,3-triazol-1-yl)phenyl]piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (18 mL) solution of 4-{[tert-butyl(dimethyl)silyl]oxy}-1-[3-(1H-1,2,3-triazol-1-yl)phenyl]piperidine (1.83 g, 5.12 mmol) was added concentrated hydrochloric acid (1030 μL, 12.5 mmol). After 6 hours, the reaction mixture was quenched with saturated aqueous sodium hydrogencarbonate solution (30 mL) and charged with ethyl acetate (30 mL). The reaction mixture was stirred vigorously for 10 minutes. The aqueous layer was extracted with more ethyl acetate (2×30 mL). The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.97 (s, 1H), 7.83 (s, 1H), 7.37 (s, 1H), 7.36 (t, J=8.1 Hz, 1H), 7.04 (d, J=8.0 Hz, 1H), 6.98 (d, J=8.5 Hz, 1H), 3.97-3.87 (m, 1H), 3.66 (dt, J=12.7, 4.7 Hz, 2H), 3.05 (ddd, J=12.7, 9.7, 3.1 Hz, 2H), 2.07-1.98 (m, 2H), 1.75-1.66 (m, 2H); LC-MS: m/z 245.2 (M+H).

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium hydrogencarbonate solution (30 mL)
  2. additioncharged with ethyl acetate (30 mL)
  3. extractionThe aqueous layer was extracted with more ethyl acetate (2×30 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washChromatography over silica gel, eluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-ee5116948e7f42278fc572a1899bc187
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

Loading…