Methanol → 3-Chloro-1-[4-(4-methoxyphenyl)piperazin-1-yl]propan-1-one

HRID 390005Notes

Reaction equation

HRID 390005 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.C(N(CC)CC)C.[Cl:24][CH2:25][CH2:26][C:27](Cl)=[O:28].CO>C(Cl)Cl>[Cl:24][CH2:25][CH2:26][C:27]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][CH:9]=2)[CH2:12][CH2:13]1)=[O:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 693643-Chloropropionyl chlorideHCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochloride

Product 1

HCID 201137083-Chloro-1-[4-(4-methoxyphenyl)piperazin-1-yl]propan-1-oneYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Methoxyphenyl)piperazine dihydrochloride (1.85 g, 6.976 mmol) was dissolved in methylene chloride. After adding triethylamine (1.9 mL, 13.952 mmol) dropwise at 0° C. and then dissolving, the mixture was stirred for 30 minutes. After adding 3-chloropropionyl chloride (0.67 mL, 6.976 mmol), the reaction solution was stirred at room temperature for 1 hour. After adding methanol, the reaction solution was extracted 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 (1.76 g, 6.224 mmol, 89.3%) was yielded as white solid.

Workup

  1. dissolutiondissolving
  2. stirringthe reaction solution was stirred at room temperature for 1 hour
  3. extractionthe reaction solution was extracted with methylene chloride
  4. customThe organic layer was dried with desiccant and
  5. filtrationthen filtered
  6. concentrationThe filtrate was concentrated
  7. custompurified by column chromatography (EtOAc/hexane, 4:1)

Sources & evidence

ORD record
ord-54bdf81123af4c76bc8d1e30633b0d8f
Source dataset
uspto-grants-2013_02
Patent number
US08383631B2

Reaction notes

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