3-Fluorobenzylamine → HCID 54724205, compound

HRID 1866977Notes

Reaction equation

HRID 1866977 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH2:15]>C(O)CCC>[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][N:15]1[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[CH:3][C:4]1=[O:9]

Participants

4

Reactant 2

HCID 668533-FluorobenzylamineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54724205HCID 54724205, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4-hydroxy-6-methyl-2-pyrone (2.5 g, 0.02 mol) and 3-fluorobenzylamine (2.5 g, 0.02 mol) in n-butanol (15.0 mL) was heated to reflux for 16 h under argon atmosphere. Butanol wad distilled in vacuo, the residue was triturated with EtOAc, cooled and filtered the precipitate. It was washed with cold EtOAc, and dried to give 0.86 g of the title compound as a pale yellow powder: 1H-NMR (CD3OD/400 MHz) δ 7.31 (m, 1H), 7.0-6.85 (m, 2H), 6.83 (d, 1H, J=9.6 Hz), 5.96 (d, 1H, j=2.0 Hz), 5.80 (d, 1H, J=2.0 Hz), 5.30 (s, 2H), and 2.24 (s, 3H); ESMS m/z 234 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h under argon atmosphere
  3. distillationButanol wad distilled in vacuo
  4. customthe residue was triturated with EtOAc
  5. temperaturecooled
  6. filtrationfiltered the precipitate
  7. washIt was washed with cold EtOAc
  8. customdried

Sources & evidence

ORD record
ord-9acbf78a8fe34c3ea01c9fbde197c554
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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