Diisopropylethylamine → 1-[4-(N-chloroacetylamino)benzoyl]-4-(4-chlorobenzyl)piperazine

HRID 1975363Notes

Reaction equation

HRID 1975363 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:24][CH2:25][C:26]([NH:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)=[O:27]>O1CCCC1>[Cl:24][CH2:25][C:26]([NH:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([N:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:8][CH2:9]2)=[O:34])=[CH:31][CH:30]=1)=[O:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1348264-ChlorobenzylpiperazineHCID 133056934-Chloroacetylaminobenzoic acid chloride

Product 1

HCID 190995101-[4-(N-chloroacetylamino)benzoyl]-4-(4-chlorobenzyl)piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.18 g of 4-chlorobenzylpiperazine are dissolved in 40 ml of absolute tetrahydrofuran. With stirring, 1.73 g of Hunig base and 2.64 g of 4-chloroacetylaminobenzoic acid chloride are added thereto in succession. The internal temperature rises to approximately 38°. After 30 minutes, the solution is concentrated by evaporation. The oily residue is digested with water, yielding 1-[4-(N-chloroacetylamino)benzoyl]-4-(4-chlorobenzyl)piperazine having a melting point of 205°-207°.

Workup

  1. customrises to approximately 38°
  2. concentrationthe solution is concentrated by evaporation

Sources & evidence

ORD record
ord-3544597f0f8f4ee7be2d972a26fbb7d7
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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