1-Bromo-4-phenylbutan-2-one → HCID 24952865, compound

HRID 1946966Notes

Reaction equation

HRID 1946966 reaction equation
C([NH:4][C:5]([NH2:7])=[NH:6])(=O)C.Br[CH2:9][C:10](=O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[CH2:11]([C:10]1[NH:6][C:5]([NH2:7])=[N:4][CH:9]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 126080271-Bromo-4-phenylbutan-2-oneHCID 178475102HCID 178475102, compound

Product 1

HCID 24952865HCID 24952865, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-acetylguanidine (1.34 g, 13.2 mmol) in dimethylformamide (7 ml) a solution of 1-bromo-4-phenyl-butan-2-one (1.5 g, 6.6 mmol) in dimethylformamide (7 ml) was added at 0° C. The mixture was stirred overnight at room temperature and then the solvent was evaporated. Upon addition of ethyl acetate/heptane (1:1) a white solid was formed that was filtered off and washed with ethyl acetate/heptane (1:1). After drying in vacuo the solid was dissolved in a mixture of concentrated hydrochloric acid (2 ml) and methanol (4 ml) and stirred for 2.5 hours at 85° C. The solvent was evaporated and the residue was purified by chromatography (column: Isolute Flash-NH2 from Separtis; eluent: ethyl acetate/methanol=1:1) to yield a light yellow solid (0.063 mg, 5%); MS (EI): 187.2 (M+).

Workup

  1. customthe solvent was evaporated
  2. additionUpon addition of ethyl acetate/heptane (1:1) a white solid
  3. customwas formed
  4. filtrationthat was filtered off
  5. washwashed with ethyl acetate/heptane (1:1)
  6. customAfter drying in vacuo the solid
  7. dissolutionwas dissolved in a mixture of concentrated hydrochloric acid (2 ml) and methanol (4 ml)
  8. stirringstirred for 2.5 hours at 85° C
  9. customThe solvent was evaporated
  10. customthe residue was purified by chromatography (column: Isolute Flash-NH2 from Separtis; eluent: ethyl acetate/methanol=1:1)

Sources & evidence

ORD record
ord-db7ec470858f4178b359d76863e161f2
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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