Diisopropylamine → N-(3-nitrophenyl)-2-(4-pyridin-2-ylpiperazin-1-yl)acetamide

HRID 490215Notes

Reaction equation

HRID 490215 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C(NC(C)C)(C)C.Cl[CH2:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=1)=[O:23]>C1(C)C=CC=CC=1>[N+:31]([C:27]1[CH:26]=[C:25]([NH:24][C:22](=[O:23])[CH2:21][N:10]2[CH2:9][CH2:8][N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:12][CH2:11]2)[CH:30]=[CH:29][CH:28]=1)([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 944591-(2-Pyridyl)piperazineHCID 5320662-chloro-N-(3-nitrophenyl)acetamide

Product 1

HCID 8547156N-(3-nitrophenyl)-2-(4-pyridin-2-ylpiperazin-1-yl)acetamideYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

1-(2-pyridinyl)piperazine (0.65 mL, 4.3 mmol, Aldrich) and N,N-diisopropylamine (5.0 mL) in toluene (20 mL) were treated with 2-chloro-N-(3-nitrophenyl)acetamide (750 mg, 3.49 mmol, Lancaster) and heated to 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 (sodium sulfate), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (elution with 25% ethyl acetate:hexanes) to provide 900 mg (76% yield) of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 2.62 (m, 4H), 3.24 (s, 2H), 3.56 (m, 4H), 6.63 (ddd, 1H, J=7.1, 4.7, 0.7 Hz), 6.83 (d, 1H, J=8.8 Hz), 7.52 (ddd, 1H, J=8.5, 7.1, 2.0), 7.61 (dd, 1H, J=8.5, 8.5 Hz), 7.92 (ddd, 1H, J=8.1, 2.4, 1.0 Hz), 8.04 (ddd, 1H, J=8.5, 2.4, 1.0 Hz), 8.11 (ddd, 1H, J=4.8, 1.7, 0.7 Hz), 8.70 (dd, 1H, J=2.0, 2.0 Hz), 10.27 (br s, 1H); MS (DCI/NH3) m/e 342 (M+H)+; Anal. calcd for C17H19N5O3: C, 59.81; H, 5.61; N, 20.52. Found: C, 59.61; H, 5.55; N, 20.23.

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 (sodium sulfate)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (elution with 25% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-802be5284a0e40f6865b674051c9a82f
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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