Diisopropylethylamine → 1-(4-Chloroacetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

HRID 1975348Notes

Reaction equation

HRID 1975348 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:25][CH2:26][C:27]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)=[O:28]>O1CCCC1>[Cl:25][CH2:26][C:27]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([N:13]2[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:15][CH2:14]2)=[O:35])=[CH:32][CH:31]=1)=[O:28]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazineHCID 133056934-Chloroacetylaminobenzoic acid chloride

Product 1

HCID 189463301-(4-Chloroacetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.34 g of 1-[2-(4-chlorophenyl)ethyl]piperazine and 1.57 g of Hunig base (=N-ethyldiisopropylamine) are introduced into 40 ml of tetrahydrofuran. 2.36 g of 4-chloroacetylaminobenzoic acid chloride [see J. Med. Chem. 28 (1985) 910] are added thereto in small portions. After 30 minutes at 40°, the solution is concentrated by evaporation. The residue is chromatographed over silica gel, and recrystallisation is carried out from acetone, yielding 1-(4-chloroacetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine having a melting point of 146°-147°.

Workup

  1. concentrationthe solution is concentrated by evaporation
  2. customThe residue is chromatographed over silica gel, and recrystallisation

Sources & evidence

ORD record
ord-f8283adfc9f047c78a33b75bc3011bc8
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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