Toluene → 2-[4-(2-methoxyphenyl)piperazin-1-yl]-N-(3-methylphenyl)acetamide

HRID 490159Notes

Reaction equation

HRID 490159 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C([N:18]([CH2:22][CH3:23])[CH:19]([CH3:21])[CH3:20])(C)C.C(OCC)(=[O:26])C.[C:30]1([CH3:36])C=CC=[CH:32][CH:31]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:23][C:22]([NH:18][C:19]2[CH:20]=[CH:32][CH:31]=[C:30]([CH3:36])[CH:21]=2)=[O:26])[CH2:11][CH2:10]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 13461-(2-Methoxyphenyl)piperazineHCID 8857Ethyl Acetate2×HCID 81531Diisopropylethylamine

Product 1

HCID 26536402-[4-(2-methoxyphenyl)piperazin-1-yl]-N-(3-methylphenyl)acetamideYield 83%

Conditions

Temperature
60 °C

Procedure

1-(2-methoxyphenyl)piperazine, (Aldrich, 1.50 g, 7.80 mmol) and N,N-diisopropylethylamine (2.0 mL) in toluene (30 mL) were treated with the product from Example 1A (1.12 g, 4.90 mmol) and heated at 60° C. for 18 hours. The mixture was allowed to cool to room temperature, transferred to a separatory funnel and washed with saturated aqueous sodium bicarbonate. The organic phase was dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (elution with 85% hexanes:ethyl acetate then 50% hexanes:ethyl acetate) to provide 1.39 g (83% yield) of the title compound as a yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 2.28 (s, 3H), 2.67 (m, 4H), 3.03 (m, 4H), 3.17 (s, 2H), 3.77 (s, 3H), 6.89 (m, 5H), 7.18 (dd, 1H, J=7.8, 7.8 Hz), 7.44 (m, 2H), 9.64 (br s, 1H); MS (DCI/NH3) m/e 340 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. customtransferred to a separatory funnel
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (
  8. washelution with 85% hexanes

Sources & evidence

ORD record
ord-0a2f41b0789a4907b4221b8d09e65b13
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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