Hexylamine → HCID 18539322, compound

HRID 412783Notes

Reaction equation

HRID 412783 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:12]([NH2:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH3:19][C:20]([CH3:23])([O-])[CH3:21].[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:18]([CH2:2][CH2:1][CH2:5][CH2:6][CH2:7][CH3:8])[C:12]2[CH:17]=[CH:16][C:15]([C:20]([CH3:23])([CH3:21])[CH3:19])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8102HexylamineHCID 775951-Bromo-4-tert-butylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 18539322HCID 18539322, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

According to the general procedure B, 4-tert-butylbromobenzene (214 mg, 1.00 mmol) reacted with n-hexylamine (66 μl, 0.50 mmol) using 1 mol % of Pd(OAc)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (116 mg, 1.21 mmol) in toluene at 100° C. for 4 h to give the title compound (182 mg, 99%) as an oil: 1H-NMR (400 MHz, CDCl3): δ 7.17 (d, 4H, J=8.4Hz), 6.82 (d, 4H, J=8.8 Hz), 3.55 (t, 2H, J=7.2 and 8.0 Hz), 1.57 (m, 2H), 1.22 (s, 18H), 0.79 (t, 3H, J=6.4 and 6.8 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 145.68, 143.41, 125.93, 120.20, 52.38, 34.06, 31.67, 31.49, 27.55, 26.78, 22.70, 14.05. GC/MS(EI): m/z 365 (M+). Anal. Calcd for C26H39N: C, 85.42; H, 10.75; N, 3.83. Found: C,85.22; H, 10.82; N, 3.86.

Workup

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

Sources & evidence

ORD record
ord-4c48852a10bb4498996e0ea7f5eb2ed9
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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