1,2-Dichloroethane → 1-[2-(4-Nitrophenyl)ethyl]-4-[2-(4-nitrophenyl)propanoyl]piperazine

HRID 1519567Notes

Reaction equation

HRID 1519567 reaction equation
C(Cl)CCl.[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=O)=[CH:10][CH:9]=1)([O-:7])=[O:6].CCN(C(C)C)C(C)C.Cl.[N+:29]([C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:34][CH:33]=1)([O-:31])=[O:30]>C(Cl)Cl.C(OCC)(=O)C>[N+:29]([C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][N:40]2[CH2:41][CH2:42][N:43]([C:15](=[O:17])[CH:14]([C:11]3[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][CH:12]=3)[CH3:18])[CH2:44][CH2:45]2)=[CH:34][CH:33]=1)([O-:31])=[O:30]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 892442-(4-Nitrophenyl)propionic acidHCID 666440061-[2-(4-Nitrophenyl)ethyl]piperazine hydrochloride

Product 1

HCID 866944681-[2-(4-Nitrophenyl)ethyl]-4-[2-(4-nitrophenyl)propanoyl]piperazineYield 60.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC (113 mg, 0.591 mmol) was added to a solution of 2-(4-nitrophenyl) propionic acid (92 mg, 0.473 mmol), Hunig's Base (0.083 ml, 0.473 mmol) and 1-[2-(4-Nitrophenyl)ethyl]piperazine hydrochloride (107 mg, 0.394 mmol) in 5 ml DCM and stirred at room temperature for 3 hours. The crude mixture was diluted with ethyl acetate and washed with saturated solution of NH4Cl, brine, dried over sodium sulfate, filtered and concentrated. Residue was purified by prep-TLC plate with 5% (NH4OH:MeOH 9:1) in DCM to yield 1-[2-(4-nitrophenyl)ethyl]-4-[2-(4-nitrophenyl)propanoyl]piperazine (100 mg, 0.24 mmol). 1H-NMR (500 MHz, DMSO) δ ppm 8.19 (d, J=9 Hz, 2H), 8.11 (d, J=9 Hz, 2H), 7.54 (d, J=9.Hz, 2H), 7.48 (d, J=9.Hz, 2H), 4.33 (q, 1H), 3.39-3.48 (m, 3H), 3.26-3.42 9 m, 2H), 2.82 (t, J=7.0 Hz, 2H), 2.5 (b, 1H), 2.35-2.40 (m, 2H), 2.26 (b, 1H), 2.0 (b, 1H), 1.30 (d, J=7 Hz, 3H).

Workup

  1. washwashed with saturated solution of NH4Cl, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customResidue was purified by prep-TLC plate with 5% (NH4OH:MeOH 9:1) in DCM

Sources & evidence

ORD record
ord-094b15e954984f8591fbbef34684b519
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

Loading…