Diisopropylethylamine → 1-{4-[N-(2-isopropyloxyethyl)-N-methoxyacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]-piperazine hydrochloride

HRID 1975359Notes

Reaction equation

HRID 1975359 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.[CH3:40][O:41][CH2:42][C:43](Cl)=[O:44]>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:43](=[O:44])[CH2:42][O:41][CH3:40])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 98455471-[4-(2-Isopropyloxyethyl)aminobenzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine

Product 1

HCID 190995121-{4-[N-(2-isopropyloxyethyl)-N-methoxyacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]-piperazine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5 g of 1-{4-[N-(2-isopropyloxyethyl)amino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine (Example 1) are dissolved in 50 ml of absolute tetrahydrofuran and cooled to 3° with stirring. There are added thereto 1.8 g of Hunig base and then, dropwise, within a period of 5 minutes, a solution of 1.38 g of methoxyacetyl 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 yield 1-{4-[N-(2-isopropyloxyethyl)-N-methoxyacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]-piperazine hydrochloride having a melting point of 149°-151°.

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-8f369e10f1484742b501547d87fe692d
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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