Sulfuric Acid → HCID 66598527, compound

HRID 1038511Notes

Reaction equation

HRID 1038511 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:19]=[C:18]([CH2:20][CH2:21][CH3:22])[C:13]([C:14]([NH:16][CH3:17])=[O:15])=[CH:12][N:11]=2)[CH2:6][CH2:5]1.S(=O)(=O)(O)O.[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[C:28]([O:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:19]=[C:18]([CH2:20][CH2:21][CH3:22])[C:13]([C:14]([NH:16][CH3:17])=[O:15])=[CH:12][N:11]=2)[CH2:8][CH2:9]1)(=[O:30])[CH3:29]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 66598065HCID 66598065, compound

Product 1

HCID 66598527HCID 66598527, compoundYield 91%

Procedure

6-[4-(2-Hydroxyethyl)piperazin-1-yl]-N-methyl-4-propylnicotinamide (477 mg, 1.56 mol) was dissolved in acetic anhydride (1.5 mL), added sulfuric acid (50 μL) under ice-cold conditions, and stirred at room temperature for 10 minutes. The reaction solution was concentrated in vacuo, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The title compound (496 mg (yield 91%)) was obtained as a yellow oil.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee76a17437e04b9b8b66dd7da1f336c5
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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