1H-Imidazole-1-propanamine → 6-[3-(3-imidazol-1-yl-propylamino)propoxy]-1-methyl-1H-quinolin-2-one

HRID 69027Notes

Reaction equation

HRID 69027 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][CH:15]=O)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]1=[O:17].OC1C=C2C(=CC=1)N(C)C(=O)C=C2.[NH2:31][CH2:32][CH2:33][CH2:34][N:35]1[CH:39]=[CH:38][N:37]=[CH:36]1.[BH4-].[Na+]>CO.O>[N:35]1([CH2:34][CH2:33][CH2:32][NH:31][CH2:15][CH2:14][CH2:13][O:12][C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[N:2]([CH3:1])[C:3](=[O:17])[CH:4]=[CH:5]3)[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

7

Reactant 4

HCID 787361H-Imidazole-1-propanamineHCID 4311764Sodium borohydrideHCID 128032046-Hydroxy-1-methylquinolin-2(1H)-oneHCID 86762695HCID 86762695, compound

Product 1

HCID 679851386-[3-(3-imidazol-1-yl-propylamino)propoxy]-1-methyl-1H-quinolin-2-oneYield 11.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

3-(1-Methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propionaldehyde (127.5 mg) prepared from 6-hydroxy-1-methylquinolin-2(1H)-one and N-(3-aminopropyl) imidazole (82.9 mg) were added to methanol (10 ml). The mixture was stirred at room temperature for 7 hours. The mixture was cooled to 0° C., and sodium borohydride (31.4 mg) was added thereto. The mixture was further stirred at room temperature overnight. Water was added to the reaction mixture and methanol was distilled off under reduced pressure. The residue was subjected to extraction using dichloromethane. The organic layer was washed with saturated saline, dried with anhydrous sodium sulfate, and was condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:0→4:1). The purified product was condensed under reduced pressure to give the title compound (21 mg) as a yellow oil.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe mixture was further stirred at room temperature overnight
  3. distillationwas distilled off under reduced pressure
  4. extractionThe residue was subjected to extraction
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried with anhydrous sodium sulfate
  7. customcondensed under reduced pressure
  8. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:0→4:1)
  9. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-a8548111fc5840c8a133afb90b1444d8
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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