Triethylamine → 2-((Tetrahydropyran-4-yl)methyl)benzoxazole

HRID 74264Notes

Reaction equation

HRID 74264 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=CC=1[N+]([O-])=O.[O:20]1CCC(CN)[CH2:22][CH2:21]1.C(N(CC)CC)C.[H][H]>[C].[Pd].O.C(#N)C>[O:20]1[CH2:2][CH2:7][CH:6]([CH2:5][C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:22][CH2:21]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 27732104-AminomethyltetrahydropyranHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674985822-((Tetrahydropyran-4-yl)methyl)benzoxazoleYield 103.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-(4-Fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (900 mg, 3.5 mmol) was added to an acetonitrile (5 mL) solution containing (tetrahydropyran-4-yl)methylamine (520 mg, 3.9 mmol) and triethylamine (500 mg, 4.3 mmol), and this was heated to reflux for 3 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a tetrahydrofuran solution (20 mL) of the crystals obtained was added 10% palladium-carbon (100 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred overnight at room temperature. After the reaction was finished, this was filtered through Celite, and the filtrate was concentrated to yield the title compound (790 mg, 70% yield) as a white solid.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a tetrahydrofuran solution (20 mL) of the crystals obtained
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e3dbbbdf6c54408f965337969dca70d7
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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