Benzoic Acid → 4-(3,4,5-Trifluorophenyl)aminotetrahydropyran

HRID 561179Notes

Reaction equation

HRID 561179 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:10])[C:8]=1[F:9])[NH2:5].[O:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.C(O)(=O)C1C=CC=CC=1.[Na].[BH4-].[Na+]>>[F:1][C:2]1[CH:3]=[C:4]([NH:5][CH:14]2[CH2:15][CH2:16][O:11][CH2:12][CH2:13]2)[CH:6]=[C:7]([F:10])[C:8]=1[F:9]

Participants

5

Reactant 4

HCID 243Benzoic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 27249913,4,5-TrifluoroanilineHCID 131729286sodium NaBH4

Product 1

HCID 590029984-(3,4,5-Trifluorophenyl)aminotetrahydropyranYield 41.4%

Procedure

To a mixture of 3,4,5-trifluoroaniline (3.70 g, 25.1 mmol), tetrahydro-4H-pyran-4-one (2.52 g, 25.1 mmol), and benzoic acid (3.07 g, 25.1 mmol), was added sodium NaBH4 (0.95 g, 25.1 mmol), the whole mixture was stirred at room temperature for 1.5 h. After quenching with the reaction mixture with 1 M aq. NaOH under cooling with ice, the whole mixture was extracted with Et2O. The extract was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Flash chromatography of the residue (hexane:EtOAc=3:2) gave 4-(3,4,5-trifluorophenyl)aminotetrahydropyran (2.40 g, 41%) as a white powder.

Workup

  1. customAfter quenching with the reaction mixture with 1 M aq. NaOH
  2. temperatureunder cooling with ice
  3. extractionthe whole mixture was extracted with Et2O
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e742700a7c074932902206bbe5236fda
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

Loading…