Benzylamine → N-benzyl-4-methylaniline

HRID 1354927Notes

Reaction equation

HRID 1354927 reaction equation
CC([O-])(C)C.[Na+].Cl[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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.C1(C)C=CC=CC=1>[CH2:15]([NH:22][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 7504BenzylamineHCID 78104-ChlorotolueneHCID 23676156Sodium t-butoxide

Product 1

HCID 79403N-benzyl-4-methylanilineYield 90%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

An oven dried Schlenk tube was purged with argon and charged with Pd2(dba)3 (4.6 mg, 0.005 mmol, 1.0 mol % Pd), Cy-BINAP (9.6 mg, 0.015 mmol, 1.5 mol %), and NaOtBu (135 mg, 1.4 mmol). The tube was purged with argon and charged with toluene (2 mL), 4-chlorotoluene (0.12 mL, 1.0 mmol), and benzylamine (0.165 mL, 1.5 mmol). The mixture was heated to 100° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was cooled to room temperature, diluted with ether (20 mL), filtered through celite, and concentrated in vacuo. The crude material was then purified by flash chromatography on silica gel to give 177 mg (90%) of a pale yellow oil.

Workup

  1. customAn oven dried Schlenk tube
  2. customwas purged with argon
  3. customThe tube was purged with argon
  4. customhad been completely consumed
  5. temperatureThe reaction mixture was cooled to room temperature
  6. additiondiluted with ether (20 mL)
  7. filtrationfiltered through celite
  8. concentrationconcentrated in vacuo
  9. customThe crude material was then purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e36a51c0a20b4c9ca99de093790144f5
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

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