1-(3-(Trifluoromethyl)phenyl)piperazine → 3-[4-(3-Trifluoromethylphenyl)-1-piperazinyl]propionic acid

HRID 585477Notes

Reaction equation

HRID 585477 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.Br[CH2:18][CH2:19][C:20]([O:22]CC)=[O:21].C(=O)(O)[O-].[Na+]>C(O)C>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 68320Ethyl 3-bromopropionateHCID 516892Sodium Bicarbonate

Product 1

HCID 114266053-[4-(3-Trifluoromethylphenyl)-1-piperazinyl]propionic acidYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reaction mixture of 1-(3-trifluoromethylphenyl)piperazine (510 mg, 2.2 mmol), ethyl 3-bromopropionate (500 mg, 2.7 mmol), sodium bicarbonate (300 mg, 3.5 mmol) and ethanol (15 ml) was refluxed for 3 h till the amine disappeared completely. After the mixture was filtered, the resulting solid was dissolved in 5 ml dioxane and 14 ml 5% sodium hydroxide solution. The mixture was stirred at room temperature overnight, then it was acidified with concentrated hydrogen chloride. Solid was filtered and washed with water, and then dried to give 500 mg 3-[4-(3-trifluoromethylphenyl)-1-piperazinyl]propionic acid as a white solid, mp 228-230° C.

Workup

  1. filtrationAfter the mixture was filtered
  2. dissolutionthe resulting solid was dissolved in 5 ml dioxane
  3. filtrationSolid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5e5a53d82e33487682a135c4b69e3e05
Source dataset
uspto-grants-2005_08
Patent number
US06933302B2

Reaction notes

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