1-(2-Pyridyl)piperazine → HCID 58492583, compound

HRID 2048007Notes

Reaction equation

HRID 2048007 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[F:13][C:14]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH3:27])=[C:20]2[C:15]=1[C:16](=[O:38])[C:17]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)=[C:18]([CH:28]=O)[NH:19]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:13][C:14]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH3:27])=[C:20]2[C:15]=1[C:16](=[O:38])[C:17]([C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)=[C:18]([CH2:28][N:10]1[CH2:9][CH2:8][N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:12][CH2:11]1)[NH:19]2

Participants

5

Reactant 3

HCID 944591-(2-Pyridyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 58492476HCID 58492476, compound

Product 1

HCID 58492583HCID 58492583, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Pyridyl)piperazine (551 mg, 3.38 mmol) was added to a 1,2-dichloromethane solution (20 ml) of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carbaldehyde (800 mg, 2.25 mmol) and stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (670 mg, 3.16 mmol) was added to the resulting mixture and stirred at room temperature for 4 hours. Dichloromethane was added to the resulting reaction mixture, washed with water, and then the mixture was dried over sodium sulfate. Thereafter, the solvent was removed under reduced pressure. The residue was then purified using NH silica gel column chromatography (dichloromethane:ethyl acetate=1:1). The solvent was removed under reduced pressure and the residue was recrystallized from ethyl acetate-n-hexane, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-8-propoxy-2-(4-pyridin-2-yl-piperazin-1-ylmethyl)-1H-quinolin-4-one (400 mg, yield: 35%).

Workup

  1. stirringstirred at room temperature for 4 hours
  2. washwashed with water
  3. dry with materialthe mixture was dried over sodium sulfate
  4. customThereafter, the solvent was removed under reduced pressure
  5. customThe residue was then purified
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-5222e5b6b9dc4be9a696a648fa722870
Source dataset
uspto-grants-2013_11
Patent number
US08592593B2

Reaction notes

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