Hydrochloric Acid → 2-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one

HRID 1876802Notes

Reaction equation

HRID 1876802 reaction equation
C([N:8]1[CH:17]2[CH:12]([CH:13]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:15][CH2:16]2)[N:11]([C:23](=[O:33])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl>C1COCC1.O.[Pd]>[Cl:32][C:27]1[CH:26]=[C:25]([CH2:24][C:23]([N:11]2[CH:12]3[CH:17]([CH2:16][CH2:15][CH2:14][CH:13]3[N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[NH:8][CH2:9][CH2:10]2)=[O:33])[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68777946HCID 68777946, compound

Product 1

HCID 687760732-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

1-[(4aRS,8SR,8aRS)-4-Benzyl-8-(pyrrolidin-1-yl)perhydroquinoxalin-1-yl]-2-(3,4-dichlorophenyl)ethan-1-one (244 mg, 0.50 mmol) was dissolved in THF/H2O (1:1, 50 ml), and conc. HCl (5 ml) and palladium-on-carbon (Pd/C) (Merck) (98.4 mg) were added. The mixture was stirred under 1 bar of H2 at room temperature for 30 minutes. The catalyst was filtered off and THF was evaporated off in vacuo. The aqueous phase was brought to pH 8 with NaOH (2 N) and extracted by shaking five times with CH2Cl2. The combined organic phases were dried over Na2SO4 and evaporated. The yellowish residue was purified by column chromatography over silica gel 60 (40-63 μm, (Merck) column Ø 3 cm, CH2Cl2/MeOH/NH3 9:1:0.1, l=17 cm, V=10 ml) and gave a yellow resin.

Workup

  1. filtrationThe catalyst was filtered off
  2. customTHF was evaporated off in vacuo
  3. extractionextracted
  4. stirringby shaking five times with CH2Cl2
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. customevaporated
  7. customThe yellowish residue was purified by column chromatography over silica gel 60 (40-63 μm, (Merck) column Ø 3 cm, CH2Cl2/MeOH/NH3 9:1:0.1, l=17 cm, V=10 ml)
  8. customgave a yellow resin

Sources & evidence

ORD record
ord-a582bfc4036841499e4474ff3513b026
Source dataset
uspto-grants-2012_11
Patent number
US08309725B2

Reaction notes

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