Hexylamine → N-Hexyl-2-methoxybenzenamine

HRID 412779Notes

Reaction equation

HRID 412779 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][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.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:10]([NH:16][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 8102HexylamineHCID 130112-ChloroanisoleHCID 23676156Sodium t-butoxide

Product 1

HCID 10727039N-Hexyl-2-methoxybenzenamineYield 97%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

According to the general procedure B, 2-Chloroanisole (72 mg, 0.51 mmol) reacted with n-hexylamine (80 μl, 0.60 mmol) using 1 mol % of Pd(OAc)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (58 mg, 0.60 mmol) in toluene at 100° C. to give the title compound (102 mg, 97%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 6.93 (t, 1H, J=8.0 Hz, aryl coupling J=0.9 Hz), 6.82 (d, 1H, J=8.0 Hz), 6.66-6.73 (m, 2H), 4.30 (bs, 1H), 3.89 (s, 3H), 3.17 (t, 2H, J=7.2 Hz), 1.71 (m, 2H), 1.51-1.34 (m, 6H), 0.97 (t, 3H, J=6.4 and 6.8 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.65, 138.39, 121.23, 116.03, 109.71, 109.24, 55.29, 43.63, 31.63, 29.43, 26.88, 22.58, 14.00. GC/MS(EI): m/z 207 (M+). Anal. Calcd for C13H21NO: C, 75.23; H, 10.21; N, 6.76. Found: C,75.41; H, 10.25; N, 6.69.

Workup

  1. customat 100° C.

Sources & evidence

ORD record
ord-43fed91e29304021ba867467b7655c23
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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