Acryloyl chloride → 1-{4-[N-(2-isopropyloxyethyl)-N-acryloylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride

HRID 1975360Notes

Reaction equation

HRID 1975360 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[CH:30]=[CH:29][C:11]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:16][CH2:15]2)=[O:13])=[CH:10][CH:9]=1)([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[C:40](Cl)(=[O:43])[CH:41]=[CH2:42]>O1CCCC1>[ClH:28].[CH:1]([O:4][CH2:5][CH2:6][N:7]([C:8]1[CH:30]=[CH:29][C:11]([C:12]([N:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:18][CH2:19]2)=[O:13])=[CH:10][CH:9]=1)[C:40](=[O:43])[CH:41]=[CH2:42])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 98455471-[4-(2-Isopropyloxyethyl)aminobenzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine

Product 1

HCID 190995021-{4-[N-(2-isopropyloxyethyl)-N-acryloylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3 g of 1-{4-[N-(2-isopropyloxyethyl)amino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine are dissolved in 40 ml of absolute tetrahydrofuran and cooled to 3° with stirring. There are added thereto 1.08 g of Hunig base and then, dropwise, within a period of 5 minutes, a solution of 0.65 g of acrylic acid chloride in 5 ml of absolute tetrahydrofuran. The mixture is stirred for 30 minutes at RT and concentrated by evaporation. The residue is taken up in water and ethyl acetate and the organic phase is washed until neutral with sodium hydrogen carbonate solution and water and concentrated by evaporation. The brown oil is chromatographed over silica gel. The mixture is treated with ethereal hydrochloric acid. Recrystallisation from acetone and ether yields 1-{4-[N-(2-isopropyloxyethyl)-N-acryloylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride having a melting point of 132°-134°.

Workup

  1. temperaturecooled to 3°
  2. additionThere are added
  3. stirringThe mixture is stirred for 30 minutes at RT
  4. concentrationconcentrated by evaporation
  5. washethyl acetate and the organic phase is washed until neutral with sodium hydrogen carbonate solution and water
  6. concentrationconcentrated by evaporation
  7. customThe brown oil is chromatographed over silica gel
  8. additionThe mixture is treated with ethereal hydrochloric acid
  9. customRecrystallisation from acetone and ether

Sources & evidence

ORD record
ord-763309eaa0074622901ce370d8735008
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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