Triethylamine → 1-(4-(2-(4,5-Dichloro-2-ethylphenylamino)acetyl)piperazin-1-yl)prop-2-en-1-one

HRID 588788Notes

Reaction equation

HRID 588788 reaction equation
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][C:6]([NH:10][CH2:11][C:12]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:13])=[C:5]([CH2:20][CH3:21])[CH:4]=1.CCN(CC)CC.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31]>C(Cl)Cl>[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][C:6]([NH:10][CH2:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:29](=[O:32])[CH:30]=[CH2:31])[CH2:16][CH2:15]2)=[O:13])=[C:5]([CH2:20][CH3:21])[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 1317344452-(4,5-Dichloro-2-ethylphenylamino)-1-(piperazin-1-yl)ethanone hydrochloride

Product 1

HCID 904627381-(4-(2-(4,5-Dichloro-2-ethylphenylamino)acetyl)piperazin-1-yl)prop-2-en-1-oneYield 23.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of above crude 2-(4,5-dichloro-2-ethylphenylamino)-1-(piperazin-1-yl)ethanone hydrochloride (82 mg) and Et3N (69 mg, 0.686 mmol) in DCM (3 mL) 0° C., a solution of acryloyl chloride (23 mg, 0.251 mmol) in DCM (1 mL) was added. The resulting mixture was stirred at room temperature for 1 h and then was quenched withed saturated NaHCO3 solution. The mixture was diluted with ethyl acetate, washed with saturated NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (DCM/MeOH=30:1) to afford the desired product (20 mg, 18.76% yield, 2 steps) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ: 7.11 (s, 1H), 6.58 (dd, J=10.4, 16.4 Hz, 1H), 6.54 (s, 1H), 6.36 (dd, J=1.6, 16.4 Hz, 1H), 5.79 (dd, J=1.6, 10.4 Hz, 1H), 5.08 (bs., 1H), 3.89-3.52 (m, 10H), 2.52 (q, J=7.2 Hz, 2H), 1.29-1.26 (t, J=7.6 Hz, 3H). ESI-MS m/z: 370.2[M+H]+.

Workup

  1. customwas quenched withed saturated NaHCO3 solution
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (DCM/MeOH=30:1)

Sources & evidence

ORD record
ord-e1b6cc33949d45f3a5f44b0ae0be9876
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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