p-Anisoyl chloride → 1-[2-(4-Chlorophenyl)-ethyl]-4-(4-methoxybenzoyl)piperazine

HRID 1381873Notes

Reaction equation

HRID 1381873 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.C(N(CC)CC)C.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:29](=[O:30])[C:28]3[CH:32]=[CH:33][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazine

Product 1

HCID 212752941-[2-(4-Chlorophenyl)-ethyl]-4-(4-methoxybenzoyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

22.4 g of 1-[2-(4-chlorophenyl)-ethyl]piperazine and 12.1 g of triethylamine are dissolved in 200 ml of dichloromethane, and a solution of 20.4 g of 4-methoxybenzoyl chloride in 30 ml of dichloromethane is added dropwise, while stirring, at 25°-30°. Stirring is continued overnight at room temperature and then the whole is washed in succession with 150 ml of 2N sodium hydroxide solution and with water, dried over sodium sulphate and concentrated to dryness by evaporation. The residue is crystallised from ethanol. 1-[2-(4-chlorophenyl)-ethyl]-4-(4-methoxybenzoyl)piperazine having a melting point of 105°-106° is obtained.

Workup

  1. stirringStirring
  2. washthe whole is washed in succession with 150 ml of 2N sodium hydroxide solution and with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated to dryness by evaporation
  5. customThe residue is crystallised from ethanol

Sources & evidence

ORD record
ord-f0208133054b4a7ebed56a1879bd98ad
Source dataset
uspto-grants-1989_02
Patent number
US04804661

Reaction notes

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