4-Fluorobenzylamine → HCID 22051128, compound

HRID 1832022Notes

Reaction equation

HRID 1832022 reaction equation
O[C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1>C(O)CCC>[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:16]2[C:6]([CH3:8])=[CH:7][C:2]([NH:16][CH2:15][C:14]3[CH:17]=[CH:18][C:11]([F:10])=[CH:12][CH:13]=3)=[CH:3][C:4]2=[O:9])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 22051128HCID 22051128, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4-hydroxy-6-methylpyrone (5.0 g, 0.04 mol) and 4-fluorobenzylamine (10.0 g. 0.08 mol) in n-butanol (25.0 mL) was heated to reflux for 24 hours under argon atmosphere. The resulting solution was concentrated to dryness under reduced pressure. The residue was triturated with ethyl acetate and filtered. It was thoroughly washed with ethyl acetate and dried to afford the title compound as a pale yellow powder (4.1 g. 30%). 1H-NMR (CD3OD, 400 MHz) δ 7.33 (q, 2H), 7.04 (m, 5H), 5.85 (d, 1H, J=2.0 Hz), 5.44 (d, 2H, J=2.4 Hz), 5.20 (s, 1H), 4.29 (s, 2H), 2.17 (s, 3H); ES-HRMS m/z 341.1488 (M+H calculated for C20H19N2OF2 requires 341.1460).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours under argon atmosphere
  3. concentrationThe resulting solution was concentrated to dryness under reduced pressure
  4. customThe residue was triturated with ethyl acetate
  5. filtrationfiltered
  6. washIt was thoroughly washed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-80c611e1e6d342b7ad1a007e1eeb4f51
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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