1-Isopropylpiperazine → HCID 58032141, compound

HRID 2167278Notes

Reaction equation

HRID 2167278 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH2:6][C@@H:5]1[CH3:28])(=[O:3])[CH3:2].[CH:29]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)([CH3:31])[CH3:30].C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:35]3[CH2:36][CH2:37][N:32]([CH:29]([CH3:31])[CH3:30])[CH2:33][CH2:34]3)=[CH:11][CH:12]=2)[CH:7]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH2:6][CH:5]1[CH3:28])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 780131-IsopropylpiperazineHCID 66624828HCID 66624828, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 58032141HCID 58032141, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

88.9 mg of (2S,4R)-1-acetyl-6-bromo-2-methyl-4-[(4-morpholinophenyl)amino]-1,2,3,4-tetrahydroquinoline was dissolved in 4 mL of toluene, and 142.5 μL of 1-isopropylpiperazine, 9.2 mg of tris(dibenzylideneacetone)dipalladium(0), 6.0 mg of (2-biphenyl)-di-tert-butylphosphine, and 38.4 mg of tert-butoxysodium were sequentially added to the solution. The mixture was heated to reflux for 12 hours. The reaction liquid was cooled, and then was filtered through Celite. The filtrate was washed with chloroform, water was added to the filtrate, and the mixture was extracted three times with chloroform. The extraction product was washed with saturated brine, dehydrated over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (chloroform:methanol=10:1), and then was recrystallized from ethyl acetate-hexane. Thus, 22.0 mg (22.4%, cis:trans=9:1) of the title compound was obtained as a pale yellow crystalline powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 12 hours
  3. customThe reaction liquid
  4. temperaturewas cooled
  5. filtrationwas filtered through Celite
  6. washThe filtrate was washed with chloroform, water
  7. additionwas added to the filtrate
  8. extractionthe mixture was extracted three times with chloroform
  9. washThe extraction product was washed with saturated brine
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting residue was purified
  12. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7a321f7a0ed14f279bf8976a150420ee
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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