Phenacylamine → HCID 21841526, compound

HRID 1416535Notes

Reaction equation

HRID 1416535 reaction equation
[CH2:1]([Mg]Br)[CH:2]([CH3:4])[CH3:3].CC[O:9]CC.[CH2:12]1[CH2:16]OC[CH2:13]1.[NH2:17][CH2:18][C:19]([C:21]1C=CC=[CH:23][CH:22]=1)=O.[Cl-].[NH4+]>C1COCC1>[OH:9][C:2]([C:4]1[CH:23]=[CH:22][CH:21]=[CH:19][C:18]=1[NH2:17])([CH3:3])[CH2:1][CH:12]([CH3:16])[CH3:13]

Participants

6

Reactant 4

HCID 11952PhenacylamineHCID 25517Ammonium ChlorideHCID 21868444Ether tetrahydrofuranHCID 178418816HCID 178418816, compound

Product 1

HCID 21841526HCID 21841526, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

After dissolving 44.4 mmol of isobutylmagnesium bromide (2M ether solution) in 30 ml of a solvent mixture: ether/THF=1:1, a solution containing 2.0 g (14.8 mmol) of 2-aminoacetophenone in 10 ml of THF was added dropwise while maintaining the internal temperature at 15° C. or less. After stirring at 15° C. for an hour, the reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 2.9 g of the desired product as an yellow oil. Yield was quantitative.

Workup

  1. additionwas added dropwise
  2. temperaturewhile maintaining the internal temperature at 15° C. or less
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3752248536144c4daacb1482bb88050d
Source dataset
uspto-grants-1999_06
Patent number
US05914344

Reaction notes

Loading…