Benzylamine → N-Benzyl-4-methoxyaniline

HRID 412785Notes

Reaction equation

HRID 412785 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=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]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 121674-ChloroanisoleHCID 23676156Sodium t-butoxide

Product 1

HCID 519413N-Benzyl-4-methoxyanilineYield 93%

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, 4-chloroanisole (73 mg, 0.51 mmol) reacted with benzylamine (68 mg, 0.63 mmol) using 1 mol % of Pd(dba)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (60 mg, 0.63 mmol) in toluene at 100° C. for 4 h to give the title compound (100 mg, 93%) as a solid: 1H-NMR (500 MHz, CDCl3): δ 6.63 (d, 2H, J=8.84 Hz), 6.81 (d, 2H, J=8.83 Hz), 7.41-7.35 (m, 4H), 7.30 (t, 1H, J=7.08 and 7.03 Hz), 4.31 (s, 2H), 3.77 (s, 3H). 13C{1H}-NMR (125 MHz, CDCl3): δ 152.18, 142.42, 139.66, 128.56, 127.52, 127.14, 114.89, 114.09, 55.78, 49.23. GC/MS(EI): m/z 213 (M+).

Workup

  1. customat 100° C.
  2. customfor 4 h

Sources & evidence

ORD record
ord-102888443f3045c084418ea405022f1e
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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