Triethylamine → 2-(4-nitrophenyl)-N-(2-(4-phenylpiperazin-1-yl)ethyl)acetamide

HRID 1516784Notes

Reaction equation

HRID 1516784 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH2:15])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[N+:23]([C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33](Cl)=[O:34])=[CH:28][CH:27]=1)([O-:25])=[O:24]>C(Cl)Cl>[N+:23]([C:26]1[CH:27]=[CH:28][C:29]([CH2:32][C:33]([NH:15][CH2:14][CH2:13][N:10]2[CH2:9][CH2:8][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][CH2:11]2)=[O:34])=[CH:30][CH:31]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 47425032-(4-Phenylpiperazin-1-yl)ethan-1-amineHCID 6452210Benzeneacetyl chloride, 4-nitro-

Product 1

HCID 222613202-(4-nitrophenyl)-N-(2-(4-phenylpiperazin-1-yl)ethyl)acetamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-Phenyl-piperazin-1-yl)-ethylamine 4a (0.5 g, 2.44 mmol) and Et3N (0.34 g, 3.41 mmol) in 40 mL of dry CH2Cl2 under nitrogen at 0° C. was added a solution (4-Nitro-phenyl)-acetyl chloride (0.58 g, 2.92 mmol). The temperature was allowed to rise to room temperature, the mixture was stirred for 2 h, and then washed with water. The aqueous layer was extracted with dichloromethane. The combined organic phase was washed with saturated sodium chloride, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography over silica gel (EtOAc) to produce 26a: 0.8 g, (89% yield) as a white solid (mp: 138-139° C.). 1H NMR (CDCl3, 400 MHz): δ 2.52 (2H, t, J=5.6, CH2—CH2NH), 2.57 (4H, t, J=5.2, (CH2)2N—), 3.11 (4H, t, J=5.2, (CH2)2—NPh), 3.36-3.34 (2H, m, CH2—NHCO), 3.65 (2H, s, CH2Ar), 6.19 (1H, bs, NHCO), 6.86-6.91 (3H, m, ArH), 7.25-7.29 (2H, m, ArH), 7.47 (2H, d, J=8.8, ArH), 8.16-8.19 (2H, m, ArH).

Workup

  1. customto rise to room temperature
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washThe combined organic phase was washed with saturated sodium chloride
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography over silica gel (EtOAc)

Sources & evidence

ORD record
ord-185016e6ac8a4575bc9bc839f0da2bd6
Source dataset
uspto-grants-2012_07
Patent number
US08227604B2

Reaction notes

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