Phenethyl bromide → HCID 54089695, compound

HRID 1978422Notes

Reaction equation

HRID 1978422 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10](=[O:25])[CH:11]=[CH:12][C:13]2[S:23][C:22]3[N:24]4[C:15](=[CH:16][N:17]=[C:18]4[CH:19]=[CH:20][CH:21]=3)[CH:14]=2)[CH2:5][CH2:4]1.[CH2:26](Br)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>C(O)C.C(=O)([O-])O.[Na+]>[CH2:26]([N:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10](=[O:25])[CH:11]=[CH:12][C:13]2[S:23][C:22]3[N:24]4[C:15](=[CH:16][N:17]=[C:18]4[CH:19]=[CH:20][CH:21]=3)[CH:14]=2)[CH2:5][CH2:4]1)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 7666Phenethyl bromide2×HCID 8471TriethylamineHCID 70243724HCID 70243724, compound

Product 1

HCID 54089695HCID 54089695, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

In 10 ml of ethanol was suspended 0.998 g (2.5 mM) of N-(piperidin-4-yl)-3-(5-thia-1,8b-diazaacenaphthylen-4-yl)acrylamide dihydrochloride as well as 0.703 g (3.8 mM) of phenethyl bromide, followed by addition of 1.74 ml (12.5 mM) of triethylamine, and the mixture was refluxed for 5 hours. To this reaction mixture was further added 0.070 g (0.38 mM) of phenethyl bromide, and the mixture was refluxed overnight. This reaction mixture was diluted with 5% aqueous solution of sodium hydrogen carbonate and extracted with dichloromethane. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over Na2SO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-methanol=4/1) and concentrated and the residue was crystallized from ether to provide the title compound.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. temperaturethe mixture was refluxed overnight
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over Na2SO4
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate-methanol=4/1)
  8. concentrationconcentrated
  9. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-30fac37b0b2a41ea834520d389e46257
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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