Triethylamine → 1-(2-quinolinyl)-4-Piperidinol

HRID 2207773Notes

Reaction equation

HRID 2207773 reaction equation
C(N(CC)CC)C.Cl[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[NH:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]1>CN(C=O)C.O>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[N:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 119282-ChloroquinolineHCID 79341Piperidin-4-ol

Product 1

HCID 405164181-(2-quinolinyl)-4-PiperidinolYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Triethylamine (2.9 g, 29.6 mmol), 2-chloro-quinoline (purchased from Alfa Aesar™) (2.4 g, 14.8 mmol) and piperidin-4-ol (1.5 g, 14.8 mmol) were dissolved in DMF (20 mL). The resulting mixture was heated to 100° C. overnight. The mixture was then diluted with water (20 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were combined and washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 70% EtOAc in petroleum ether) to give 1-(quinolin-2-yl)piperidin-4-ol (2.0 g, 8.7 mmol, 60% yield) as white solid. ESI-MS (M+1): 229 calc. for C14H16N2O 228.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel (20% to 70% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-2e44f31cc2db4c10b359e075d7c5032f
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

Loading…