Benzylamine → 4-(Benzylamino)benzonitrile

HRID 412787Notes

Reaction equation

HRID 412787 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[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]>[C:6]([C:5]1[CH:8]=[CH:9][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)#[N:7]

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 121634-ChlorobenzonitrileHCID 23676156Sodium t-butoxide

Product 1

HCID 99425094-(Benzylamino)benzonitrileYield 77.8%

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-chlorobenzonitrile (69 mg, 0.50 mmol) reacted with benzylamine (54 mg, 0.50 mmol) using 1 mol % of Pd(dba)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (58 mg, 0.60 mmol) in toluene at 50° C. for 24 h to give the title compound (81 mg, 76%) as a solid: 1H-NMR (300 MHz, CDCl3): δ 7.41 (d, 2H, J=8.7 Hz), 7.36 (m, 5H), 6.61 (d, 2H, J=8.4 Hz), 4.73 (bs, 1H), 4.39 (d, 2H, J=5.4 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 151.05, 137.76, 133.67, 128.82, 127.64, 127.26, 120.36, 112.36, 98.99, 47.42. GC/MS(E): m/z 208 (M+), 209.

Workup

  1. customat 50° C.
  2. customfor 24 h

Sources & evidence

ORD record
ord-9f5bb33202884880a248776fdd2b11f2
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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