Sulfuric Acid → Benzamide

HRID 1872469Notes

Reaction equation

HRID 1872469 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](C(N2C(CC3CCCCC3)C(=O)N3CC4C=CC=CC=4CC3C2=O)C(NCCC2C=CC(F)=CC=2)=O)=[CH:5][CH:4]=1)#[N:2].S(=O)(=O)(O)[OH:46]>>[C:1]([NH2:2])(=[O:46])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 18689596HCID 18689596, compound

Product 1

HCID 2331Benzamide

Procedure

This compound was prepared by stirring 2-(4-cyano-phenyl)-2-(3-cyclohexylmethyl-1,4-dioxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-2-yl)-N-[2-(4-fluoro-phenyl)-ethyl]-acetamide (305 mg, 0.51 mmol) in 10 ml of concentrated sulfuric acid. After 1 hour the solution was poured into 40 g of ice. The ice melted and the white solid was filtered, dried, and the crude product was purified by flash chromatography (1:20 methanol/dichloromethane; Rf =0.25) to give 60 mg (20%) of 4-{(3-cyclohexylmethyl-1,4-dioxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-2-yl)-[2-4-fluoro-phenyl)-ethylcarbamoyl]-methyl}-benzamide.

Workup

  1. customThis compound was prepared
  2. filtrationthe white solid was filtered
  3. customdried
  4. customthe crude product was purified by flash chromatography (1:20 methanol/dichloromethane; Rf =0.25)

Sources & evidence

ORD record
ord-8c3c7d8d4d7145ed8396ad99ca54f738
Source dataset
uspto-grants-2000_08
Patent number
US06107274

Reaction notes

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