Methanol → HCID 23156520, compound

HRID 228512Notes

Reaction equation

HRID 228512 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:17]=1[CH:18]=O.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[BH4-].[Na+].C(OCC)(=O)C.[CH3:39][OH:40]>O>[CH3:39][O:40][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:17]=1[CH2:18][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

7

Reactant 5

HCID 887MethanolHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 23078271HCID 23078271, compound

Product 1

HCID 23156520HCID 23156520, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylbenzaldehyde (88.6 mg) was dissolved in methanol (5 ml). Piperidine (250 mg) was then added to the solution, and the mixture was stirred at room temperature for 10 min. Further, sodium borohydride (17.5 mg) was added thereto, and the mixture was stirred at room temperature for 20 min. Ethyl acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-hexane to give the title compound (71 mg, yield 66%).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-28420c1ac7a4402d9b643411e76462c5
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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