Hydrochloric Acid → HCID 23159888, compound

HRID 2110891Notes

Reaction equation

HRID 2110891 reaction equation
[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[H-].[Na+].Cl[CH2:15][C:16]1[CH:35]=[CH:34][C:19]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.[I-].[Na+].[OH-].[Na+].Cl>CN(C)C=O.C(OCC)(=O)C.O1CCCC1.CO>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:15][C:16]1[CH:35]=[CH:34][C:19]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 962892-Methyl-1,2,3,4-tetrahydroquinolineHCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoate

Product 1

HCID 23159888HCID 23159888, compoundYield 47%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl-1,2,3,4-tetrahydroquinoline (0.19 mL, 1.32 mmol) in N,N-dimethylformamide (3.5 mL) was added sodium hydride (60% in oil, 53 mg, 1.32 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 10 min. Methyl 3-(4-{[4-(chloromethyl)benzyl]oxy}phenyl)propanoate (0.35 g, 1.10 mmol) and sodium iodide (0.20 g, 1.32 mmol) were added to the obtained mixture and the mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with ethyl acetate, and the mixture washed with 5% aqueous potassium hydrogensulfate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an oil. Then, a mixture of the obtained oil, 1 N aqueous sodium hydroxide solution (2.2 mL), methanol (4.0 mL) and tetrahydrofuran (8.0 mL) was stirred at room temperature for 2 hr. The reaction mixture was adjusted to pH 7 with 1 N hydrochloric acid, and diluted with ethyl acetate. The mixture washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/2) to give the title compound (0.21 g, yield 47%) as beige crystals. MS (APCI−): 414 (M−H).

Workup

  1. stirringthe mixture was stirred at the same temperature for 10 min
  2. stirringthe mixture was stirred at room temperature for 18 hr
  3. washthe mixture washed with 5% aqueous potassium hydrogensulfate solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil
  7. stirringwas stirred at room temperature for 2 hr
  8. washThe mixture washed with water and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-c07bfe8053b74744bc32668b4106eefc
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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