Triethylamine → 1-[2-(4-Chlorophenyl)-ethyl]-4-(3-dimethylaminobenzoyl)-piperazine

HRID 1381879Notes

Reaction equation

HRID 1381879 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:16][CH:15]=1.C(N(CC)CC)C.[OH-].[Na+]>C(Cl)Cl>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][N:25]([C:6](=[O:7])[C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([N:2]([CH3:12])[CH3:1])[CH:4]=3)[CH2:26][CH2:27]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 70103423-Dimethylaminobenzoyl chlorideHCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazine

Product 1

HCID 212753321-[2-(4-Chlorophenyl)-ethyl]-4-(3-dimethylaminobenzoyl)-piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 6.51 g of 3-dimethylaminobenzoyl chloride in 130 ml of methylene chloride is added dropwise, over a period of 10 minutes, to a solution, stirred at room temperature, of 7.97 g of 1-[2-(4-chlorophenyl)-ethyl]-piperazine and 3.6 g of triethylamine in 150 ml of methylene chloride. The reaction mixture is stirred overnight at room temperature, diluted with methylene chloride, rendered alkaline with 2N NaOH and washed with water, dried over sodium sulphate and concentrated to dryness by evaporation. The residue is recrystallised from ethanol. 1-[2-(4-chlorophenyl)-ethyl]-4-(3-dimethylaminobenzoyl)-piperazine having a melting point of 110°-112° is thus obtained.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated to dryness by evaporation
  4. customThe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-dc287ae77acc4378a6d5872e21119552
Source dataset
uspto-grants-1989_02
Patent number
US04804661

Reaction notes

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