Phenacyl bromide → HCID 86697897, compound

HRID 338085Notes

Reaction equation

HRID 338085 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH2:11]([NH:14][CH2:15][CH:16]=[CH2:17])[CH:12]=[CH2:13].Cl.[NH2:19][OH:20]>N1C=CC=CC=1.C(#N)C>[CH2:11]([N:14]1[CH2:15][CH:16]2[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)([NH:19][O:20][CH2:17]2)[CH2:2]1)[CH:12]=[CH2:13]

Participants

6

Reactant 3

HCID 6259Phenacyl bromideHCID 31279DiallylamineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 86697897HCID 86697897, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Alpha-bromoacetophenone (77.5 g, 389.36 mmol) is added to a rapidly stiffing solution of acetonitrile (1 L) at 0° C. To this solution is added in a drop wise fashion, diallylamine (98.40 mL, 798.18 mmol) over 10 min. The mixture is warmed to room temperature and stirred for 96 h. The solvent is removed under reduced pressure and the residue is dissolved in ethanol (778.71 mL). Pyridine (110.20 mL, 1.36 mmol) is added to the solution followed by hydroxylamine hydrochloride (67.64 g, 973.39 mmol). The reaction is heated to 70° C. for 4 h and then stirred overnight at RT. The solvent is removed under reduced pressure and the residue is dissolved in toluene (1 L). The reaction is heated to 120° C. and stirred overnight. The solvent is removed under reduced pressure. The product is purified via silica gel chromatography eluting with 0-100% ethyl acetate/hexanes to give the title compound as a light red oil (71.2 g, 79.4%) that is used without further purification. EI/MS (m/e): 231.0 (M+H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue is dissolved in ethanol (778.71 mL)
  3. temperatureThe reaction is heated to 70° C. for 4 h
  4. stirringstirred overnight at RT
  5. customThe solvent is removed under reduced pressure
  6. dissolutionthe residue is dissolved in toluene (1 L)
  7. temperatureThe reaction is heated to 120° C.
  8. stirringstirred overnight
  9. customThe solvent is removed under reduced pressure
  10. customThe product is purified via silica gel chromatography
  11. washeluting with 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8fd4ec4d687b443586011334c0248a59
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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