Triethylamine → 1-Methyl-3-phenyl-4-(4-chlorophenacyl) piperazine

HRID 622779

Reaction equation

HRID 622779 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1.C(N(CC)CC)C.[Cl:21][C:22]1[CH:31]=[CH:30][C:25]([C:26](=[O:29])[CH2:27]Br)=[CH:24][CH:23]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.C(Cl)(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:27][C:26]([C:25]2[CH:30]=[CH:31][C:22]([Cl:21])=[CH:23][CH:24]=2)=[O:29])[CH:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 68303p-Chlorophenacyl bromideHCID 516892Sodium BicarbonateHCID 27600091-Methyl-3-phenylpiperazine

Product 1

HCID 143023441-Methyl-3-phenyl-4-(4-chlorophenacyl) piperazineYield 95%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 14.0 g (0.08 mol) of 1-methyl-3-phenylpiperazine and 20 g (0.2 mol) of triethylamine in 160 ml of tetrahydrofuran was added dropwise a solution of 18.2 g (0.08 mol) of 4-chlorophenacyl bromide in 55 ml of chloroform. The resulting mixture was stirred at ambient temperature for 3.5 hours, poured into 50% aqueous sodium bicarbonate and extracted with chloroform. The organic extracts were combined, washed with water and saturated sodium chloride and dried over sodium sulfate. The filtrate was concentrated to dryness to give 25 g of crude 1-methyl-3-phenyl-4-(4-chlorophenacyl) piperazine. This material was used as such in the next step of the process.

Workup

  1. extractionextracted with chloroform
  2. washwashed with water and saturated sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-8f0182d5fffe48fb93eae2b4751f2601
Source dataset
uspto-grants-1988_09
Patent number
US04772705

Linked notes

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