Isopropylamine → Benzyl 3-(isopropylamino)benzoate

HRID 2097673Notes

Reaction equation

HRID 2097673 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].I[C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[CH:24]([NH2:27])([CH3:26])[CH3:25].C(C1CCCCC1=O)(=O)C(C)C>CN(C)C=O.C(OCC)(=O)C.[Cu](I)I>[CH:24]([NH:27][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])([CH3:26])[CH3:25]

Participants

8

Reactant 4

HCID 6363IsopropylamineHCID 10796Cesium carbonateHCID 114693012-(2-Methylpropanoyl)cyclohexan-1-oneHCID 22254461Benzyl 3-iodobenzoate

Product 1

HCID 58501909Benzyl 3-(isopropylamino)benzoate

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Copper iodide (1.0 equiv) and cesium carbonate (2.0 equiv) were added to a microwave vial and the vial was evacuated and filled with argon three times. Benzyl 3-iodobenzoate (4) in dry dimethylformamide (2 M), isopropylamine (2.0 equiv) and 2-isobutyrylcyclohexanone (0.2 equiv) were then added to the vial, the vial was sealed and the resulting mixture is heated to 100° C. under microwave irradiation for 2 hours. At that time, the vial was cooled to room temperature and the reaction mixture was diluted with ethyl acetate and filtered through a pad of Celite with aid of ethyl acetate. The filtrate was washed with brine (3×), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate/hexanes as elutant) to provide benzyl 3-(isopropylamino)benzoate (5).

Workup

  1. customthe vial was evacuated
  2. additionfilled with argon three times
  3. customwas sealed
  4. temperatureAt that time, the vial was cooled to room temperature
  5. filtrationfiltered through a pad of Celite with aid of ethyl acetate
  6. washThe filtrate was washed with brine (3×)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography on silica gel (ethyl acetate/hexanes as elutant)

Sources & evidence

ORD record
ord-0489d750bc604923ad4de4a788d75312
Source dataset
uspto-grants-2013_05
Patent number
US08450350B2

Reaction notes

Loading…