Hexylamine → N-n-hexyl-2,5-dimethylaniline

HRID 412781

Reaction equation

HRID 412781 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[CH2:10]([NH2:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].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]>[CH2:10]([NH:16][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 8102HexylamineHCID 32883Chloro-p-xyleneHCID 23676156Sodium t-butoxide

Product 1

HCID 10608322N-n-hexyl-2,5-dimethylanilineYield 87%

Reagents, catalysts & solvents 2

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

Procedure

According to the general procedure B, 2-Chloro-p-xylene (73 mg, 0.52 mmol) reacted with n-hexylamine (62 mg, 0.61 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 10 h to give the title compound (90 mg, 87%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 7.00 (d, 1H, J=7.2 Hz), 6.54 (d, 1H, J=7.6 Hz), 6.51 (s, 1H), 3.45 (bs, 1H), 3.20 (dd, 2H, J=6.8 and 7.2 Hz), 2.37 (s, 3H), 2.16 (s, 3H), 1.73 (m, 2H), 1.49 (m, 2H), 1.41 (m, 4H), 0.99 (t, 1H, J=6.8 and 7.2 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.23, 136.65, 129.77, 118.61, 117.14, 110.46, 43.92, 31.63, 29.56, 26.90, 22.63, 21.54, 16.98, 14.03. GC/MS(EI): m/z 205 (M+).

Workup

  1. customat 100° C.
  2. customfor 10 h

Sources & evidence

ORD record
ord-4e441fc541304b8b9da2999aff814d8c
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Linked notes

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