Potassium Carbonate → HCID 178471790, compound

HRID 1960016Notes

Reaction equation

HRID 1960016 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:14]([NH:16][CH2:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:19]1)[CH3:15].C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH2:14]([N:16]([CH2:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:19]1)[C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH3:15]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 6909582-Chloro-3-quinolinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 178464368HCID 178464368, compound

Product 1

HCID 178471790HCID 178471790, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-chloroquinoline-3-carbaldehyde (93 mg, 0.49 mmol), ethyl trans-{4-[(N-ethylamino)methyl]cyclohexyl}acetate (165 mg, 0.73 mmol) and potassium carbonate (134 mg, 0.97 mmol) in toluene (2 mL) is stirred and refluxed for 3 days. The reaction mixture is cooled to room temperature, diluted with water and ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude residue is dissolved with ethanol (1.5 mL) and treated with sodium borohydride (18 mg, 0.48 mmol). The mixture is stirred at room temperature for 2 hours. After addition of sat. ammonium chloride and water, the mixture is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give ethyl trans-[4-({N-ethyl-N-[3-(hydroxymethyl)quinolin-2-yl]amino}methyl)cyclohexyl]acetate.

Workup

  1. temperaturerefluxed for 3 days
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe crude residue is dissolved with ethanol (1.5 mL)
  7. stirringThe mixture is stirred at room temperature for 2 hours
  8. extractionthe mixture is extracted with ethyl acetate
  9. washThe combined organic layer is washed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-68de3c30ced74e5394a2171e5d64e687
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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