Hydrochloric Acid → 2-Amino-1-(4-fluorophenyl)ethan-1-one hydrochloride

HRID 874994Notes

Reaction equation

HRID 874994 reaction equation
C1N2CN3[CH2:10][N:4](C2)CN1C3.[CH:11]1[C:16]([C:17](CBr)=[O:18])=[CH:15][CH:14]=[C:13]([F:21])[CH:12]=1.[ClH:22]>C(Cl)(Cl)Cl.CCO>[ClH:22].[NH2:4][CH2:10][C:17]([C:16]1[CH:15]=[CH:14][C:13]([F:21])=[CH:12][CH:11]=1)=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 132906662-Amino-1-(4-fluorophenyl)ethan-1-one hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

Hexamethylenetetramine (1.42 g, 10.1 mmol) was added dropwise over 30 min to a solution of 2-bromo-4-fluoroacetophenone (2.0 g, 9.2 mmol) in dry CHCl3 (40 mL) at 0° C. The reaction mixture was allowed to warm up to room temperature and stirred for 16 h. After completion of the reaction the solid precipitate formed was collected by filtration and washed with CHCl3. The solid obtained was suspended in EtOH (40 mL) and conc. HCl (4 mL) was added. The mixture was heated to 80° C. for 3 h, cooled to room temperature, and the solid formed was filtered off. The clear filtrate was concentrated to afford 2-amino-1-(4-fluorophenyl)ethanone hydrochloride (1.5 g, crude) as yellow solid. MS (ESI) m/z: Calculated for C8H8FNO: 153.06. found: 153.9 (M+H)+

Workup

  1. customAfter completion of the reaction the solid precipitate
  2. customformed
  3. filtrationwas collected by filtration
  4. washwashed with CHCl3
  5. customThe solid obtained
  6. temperatureThe mixture was heated to 80° C. for 3 h
  7. temperaturecooled to room temperature
  8. customthe solid formed
  9. filtrationwas filtered off
  10. concentrationThe clear filtrate was concentrated

Sources & evidence

ORD record
ord-6057fd6783ec42f0b9de5d6c9e3dd6b5
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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