Triethylamine → 3-Chloro-1-(4-(4-chlorophenyl)piperazin-1-yl)propan-1-one

HRID 390006Notes

Reaction equation

HRID 390006 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[Cl:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl>[Cl:23][CH2:24][CH2:25][C:26]([N:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)[CH2:11][CH2:12]1)=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 693643-Chloropropionyl chlorideHCID 12212341Piperazine, 1-(4-chlorophenyl)-, hydrochloride (1:2)

Product 1

HCID 44100763-Chloro-1-(4-(4-chlorophenyl)piperazin-1-yl)propan-1-oneYield 51.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Chlorophenyl)piperazine dihydrochloride (1.88 g, 6.973 mmol) was dissolved in methylene chloride and, after slowly adding triethylamine (1.9 mL, 13.946 mmol) at 0° C., stirred for 5 minutes. After adding 3-chloropropionyl chloride (0.67 mL, 6.973 mmol), the reaction solution was stirred at room temperature. After extracting with methylene chloride, the organic layer was dried with desiccant and then filtered. The filtrate was concentrated and purified by column chromatography (EtOAc/hexane, 4:1). A target compound (1.03 g, 3.586 mmol, 51.5%) was yielded as white solid.

Workup

  1. extractionAfter extracting with methylene chloride
  2. customthe organic layer was dried with desiccant and
  3. filtrationthen filtered
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography (EtOAc/hexane, 4:1)

Sources & evidence

ORD record
ord-58d370db6741414596d3ab6550e626c0
Source dataset
uspto-grants-2013_02
Patent number
US08383631B2

Reaction notes

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