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

HRID 74263Notes

Reaction equation

HRID 74263 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)=C[C:3]=1[N+]([O-])=O.[O:20]1CCC(CCN)[CH2:22][CH2:21]1.C(N(CC)CC)C.[H][H]>[C].[Pd].O.C(#N)C>[O:20]1[CH2:3][CH2:2][CH:7]([CH2:6][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 27731982-(Oxan-4-yl)ethan-1-amineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674986762-(2-(Tetrahydropyran-4-yl)ethyl)benzoxazoleYield 62.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-(4-Fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (800 mg, 3.1 mmol) was added to an acetonitrile (5 mL) solution containing 2-(tetrahydropyran-4-yl)ethylamine (520 mg, 3.9 mmol) and triethylamine (500 mg, 3.9 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 complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (450 mg, 43% yield) as a syrup.

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
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-03e46c74cfcc46ce80ee728acd94820c
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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