Hydrochloric Acid → HCID 57785890, compound

HRID 1399359Notes

Reaction equation

HRID 1399359 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]2=[N:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:17]=3[N:13]2[CH2:12][CH2:11][N:10]1C(OC(C)(C)C)=O.Cl>C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]2=[N:15][C:16]3[C:17](=[C:18]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH:19]=[CH:20][CH:21]=3)[N:13]2[CH2:12][CH2:11][NH:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57786115HCID 57786115, compound

Product 1

HCID 57785890HCID 57785890, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of tert-butyl 1-(2,4-dichlorophenyl)-6-(diethylamino)-3,4-dihydropyrazino[1,2-a]benzimidazole-2(1H)-carboxylate (244 mg, 0.499 mmol) and hydrochloric acid (4M, ethyl acetate solution, 5 mL) was stirred at room temperature for 1 h. The mixture was diluted with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 40% ethyl acetate/n-hexane mixture to give a colorless amorphous solid (172 mg, 0.443 mmol, 89%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a 40% ethyl acetate/n-hexane mixture

Sources & evidence

ORD record
ord-7eaf36f63d06428b938c1bb27ee5b347
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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