Benzylamine → Benzylaniline

HRID 412788Notes

Reaction equation

HRID 412788 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=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]>[C:2]1([NH:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 7964ChlorobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 66028BenzylanilineYield 92%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

According to the general procedure A, chlorobenzene (58 mg, 0.51 mmol) reacted with benzylamine (68 mg, 0.64 mmol) using 1 mol % of Pd(dba)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (59 mg, 0.60 mmol) in toluene at 100° C. for 5 h to give the title compound (85 mg, 92%) as an oil. GC/MS(EI): m/z 183 (M+), 184.

Workup

  1. customat 100° C.
  2. customfor 5 h

Sources & evidence

ORD record
ord-d69ab271b491437888ce6027345687d8
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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