Triethylamine → N-[2-(4-Nitro-phenyl)-ethyl]-N-[2-(4-phenyl-piperazin-1-yl)-ethyl]-propionamide

HRID 1516786Notes

Reaction equation

HRID 1516786 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(CC)CC.[C:34](Cl)(=[O:37])[CH2:35][CH3:36]>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:19][CH2:20]2)[C:34](=[O:37])[CH2:35][CH3:36])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 22261321[2-(4-Nitro-phenyl)-ethyl]-[2-(4-phenyl-piperazin-1-yl)-ethyl]-amine

Product 1

HCID 22261339N-[2-(4-Nitro-phenyl)-ethyl]-N-[2-(4-phenyl-piperazin-1-yl)-ethyl]-propionamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [2-(4-nitro-phenyl)-ethyl]-[2-(4-phenyl-piperazin-1-yl)-ethyl]-amine 27a (0.375 g, 1.05 mmol), Et3N (0.267 g, 2.64 mmol) in 25 mL of dry CH2Cl2 under nitrogen at 0° C. was added a solution of propionyl chloride (0.137 g, 1.48 mmol). The temperature was allowed to rise to room temperature, the mixture stirred for 2 h, and then washed with water. The aqueous layer was extracted with dichloromethane. The combined organic phase was dried (Na2SO4) and concentrated. The crude product was purified by column chromatography over silica gel (EtOAc/Hex=9/1) to give 28a as a colorless oil: 0.39 g (89% yield). 1H NMR (CDCl3, 400 MHz): δ 1.16 (3H, t, J=7.2, CH3), 2.38 (2H, q, J=7.2, CH2), 2.51 (2H, t, J=7.2 Hz, CH2Ar), 2.62 (4H, t, J=4.8, (CH2)2N), 2.99 (2H, t, J=7.2, CH2—CH2NCO), 3.15-3.20 (4H, m, (CH2)2NHPh, 3.32 (2H, t, J=7.2, CH2—CH2Ar), 3.58 (2H, t, J=7.2, CH2NCO), 6.83-6.93 (3H, m, ArH), 7.23-7.28 (2H, m, ArH), 7.34 (1H, d, J=8.0, ArH), 7.38 (1H, d, J=8.8, ArH, 8.15 (1H, d, J=8.8, ArH), 8.18 (1H, d, J=8.4, ArH).

Workup

  1. customto rise to room temperature
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography over silica gel (EtOAc/Hex=9/1)

Sources & evidence

ORD record
ord-0411e8beb7194571bc27f3e520ac97c3
Source dataset
uspto-grants-2012_07
Patent number
US08227604B2

Reaction notes

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