Benzylamine → Tert.-butyl 4-benzylamino-2-methyl-benzoate

HRID 2235053Notes

Reaction equation

HRID 2235053 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([CH3:15])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH2:68]([NH2:75])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:68]([NH:75][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([CH3:15])[CH:3]=1)[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 53432590tert-Butyl 4-bromo-2-methylbenzoate

Product 1

HCID 68583793Tert.-butyl 4-benzylamino-2-methyl-benzoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

tert.-butyl 4-bromo-2-methyl-benzoate (12 g; 43.4 mmol), caesium carbonate (21.2 g, 65 mmol), palladium(II)-acetate (1 g, 4.45 mmol) and BINAP (2.37 g, 4.40 mmol) are suspended in 150 ml of toluene under a nitrogen atmosphere and stirred for 10 minutes at ambient temperature. Then benzylamine (5.7 ml, 52.1 mmol) is added dropwise and the mixture is heated to 100° C. for two days. The mixture is then cooled, filtered to remove undissolved matter and evaporated to dryness. The oily residue is purified by chromatography (silica gel, petroleum ether/ethyl acetate 98:2). White crystals are obtained.

Workup

  1. temperaturethe mixture is heated to 100° C. for two days
  2. temperatureThe mixture is then cooled
  3. filtrationfiltered
  4. customto remove undissolved matter
  5. customevaporated to dryness
  6. customThe oily residue is purified by chromatography (silica gel, petroleum ether/ethyl acetate 98:2)
  7. customWhite crystals are obtained

Sources & evidence

ORD record
ord-1e310f62bf6e456f851975526636ad92
Source dataset
uspto-grants-2010_05
Patent number
US07714000B2

Reaction notes

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