Diisopropylethylamine → 7-{1-[2-(2-Methylquinolin-5-yloxy)ethyl]piperidin-4-yloxy}-3,4-dihydro-1H-quinolin-2-one

HRID 1295589Notes

Reaction equation

HRID 1295589 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]3)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.Br[CH2:20][CH2:21][O:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27]([CH3:33])=[N:28]2.C(N(CC)C(C)C)(C)C>CC(O)C>[CH3:33][C:27]1[CH:26]=[CH:25][C:24]2[C:29](=[CH:30][CH:31]=[CH:32][C:23]=2[O:22][CH2:21][CH2:20][N:1]2[CH2:2][CH2:3][CH:4]([O:7][C:8]3[CH:17]=[C:16]4[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]4)=[CH:10][CH:9]=3)[CH2:5][CH2:6]2)[N:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 117371925-(2-Bromoethoxy)-2-methylquinolineHCID 179651447-(Piperidin-4-yloxy)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 179651437-{1-[2-(2-Methylquinolin-5-yloxy)ethyl]piperidin-4-yloxy}-3,4-dihydro-1H-quinolin-2-oneYield 46.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

7-(Piperidin-4-yloxy)-3,4-dihydro-1H-quinolin-2-one (0.064 g, 0.25 mmol) and 5-(2-bromoethoxy)-2-methylquinoline (0.069 g, 0.25 mmol) were mixed together in propan-2-ol (20 mL), N,N-diisopropylethylamine (0.336 g, 2.6 mmol) added and the mixture heated at reflux for 48 h. The volatiles were removed by evaporation to dryness under reduced pressure and the residue partitioned between ethyl acetate and saturated NaHCO3 aq. The phases were separated, the organic phase washed with water, dried (MgSO4) and evaporated to dryness under reduced pressure. Chromatography on SiO2, eluting with a gradient of ethyl acetate in 60–80° C. petroleum ether, gave the title compound (0.05 g, 45%) as a white solid, after trituration under 60–80° C. petroleum ether.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 48 h
  3. customThe volatiles were removed by evaporation to dryness under reduced pressure
  4. customthe residue partitioned between ethyl acetate and saturated NaHCO3 aq. The phases
  5. customwere separated
  6. washthe organic phase washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness under reduced pressure
  9. washChromatography on SiO2, eluting with a gradient of ethyl acetate in 60–80° C. petroleum ether

Sources & evidence

ORD record
ord-8b0f2b21fd8348bfb79de6df7d1f2fdb
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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