Potassium Carbonate → HCID 23291066, compound

HRID 365311Notes

Reaction equation

HRID 365311 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:13])[NH:7]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=2)[CH2:26][CH2:25]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:12][C:9]1[CH:10]=[CH:11][C:2]([O:1][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][N:27]([CH2:30][C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]=3)[CH2:26][CH2:25]2)=[C:3]2[C:8]=1[NH:7][C:6](=[O:13])[CH2:5][CH2:4]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10976036HCID 10976036, compoundHCID 23291076HCID 23291076, compound

Product 1

HCID 23291066HCID 23291066, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

After a mixture consisting of 5-hydroxy-8-methyl-1,2,3,4-tetrahydroquinolin-2-one (1.80 g, 10.2 mmol), tetra-n-butylammonium bromide (0.322 g, 1 mmol), potassium carbonate (4.146 g, 30 mmol), 1-(3-chloropropyl)-4-(2-quinolylmethyl)piperazine (3.67 g, 12.1 mmol) and N,N-dimethylformamide (40 ml) was stirred for 2 days at a bath temperature of 50° C. under an argon gas stream, the solvent was distilled off under reduced pressure. Water was added to the residue, followed by extraction with chloroform. The extract was washed with water and then dried over anhydrous magnesium sulfate. The extract was subjected to chromatography on a silica gel column (developer: chloroform/methanol=40/1) and then crystallized from ethyl acetate-n-hexane, whereby 0.773 g of the title compound was obtained as yellow leaflets (yield: 17.2%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater was added to the residue
  3. extractionfollowed by extraction with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customcrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-33bf50789633468cb7dca32a1063b6d8
Source dataset
uspto-grants-2000_10
Patent number
US06127360

Reaction notes

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