Hexylamine → HCID 12045720, compound

HRID 412773Notes

Reaction equation

HRID 412773 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[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][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 8102HexylamineHCID 121674-ChloroanisoleHCID 23676156Sodium t-butoxide

Product 1

HCID 12045720HCID 12045720, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

According to the general procedure B, 4-chloroanisole (72 mg, 0.50 mmol) reacted with n-hexylamine (80 μl, 0.60 mmol) using 2 mol % of Pd(OAc)2, 4 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (59 mg, 0.60 mmol) in toluene at 70° C. for 8 h to give the title compound (96 mg, 92%as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 6.79 (d, 2H, J=8.0 Hz), 6.60 (d, 2H, J=8.0 Hz), 3.76 (s, 3H, ArOMe), 3.07 (t, 2H, J=6.8 Hz), 1.61 (m, 2H), 1.39 (m, 2H), 1.33 (m, 2H), 0.91 (t, 3H, J=6.4 and 6.8 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 151.92, 142.77, 114.83, 114.02, 55.80, 45.04, 31.66, 29.61, 26.87, 22.62, 14.05. GC/MS(EI): m/z 207 (M+), 136. Anal. Calcd for C13H21NO: C, 75.32; H, 10.21; N, 6.76. Found: C, 75.56; H, 10.37; N, 6.78.

Workup

  1. customat 70° C.
  2. customfor 8 h

Sources & evidence

ORD record
ord-59e853d302bb4ee080df8baf9cca4956
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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