1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 19013296, compound

HRID 1729022Notes

Reaction equation

HRID 1729022 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=O)[CH:3]=[CH:2]1.[F:13][C:14]([F:28])([F:27])[C:15]1[CH:16]=[C:17]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([N:24]2[CH2:23][CH2:22][N:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:27])([F:28])[F:13])[CH:16]=3)[CH2:26][CH2:25]2)=[O:12])[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 742811H-Indole-7-carboxylic acid

Product 1

HCID 19013296HCID 19013296, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution of indole 7-carboxylic acid (3.22 g; 0.02 moles) in 30ml dimethylformamide was added N,N'-carbonyldiimidazole (3.24 g; 0.02 moles). After 45 minutes, a solution of 4-(3-(trifluoromethyl)phenyl)piperazine (5.76 g; 0.025 moles) in 10 ml DMFwas added. This was stirred for 18 hours at ambient temperature. The solvent was then concentrated off and the resulting oil was partitioned between ethyl acetate and water. The aqueous was extracted twice with ethyl acetate and the organics were washed with water and dried (saturatedNaCl, MgSO4). The desired amine was purified via flash chromatography (10% ethyl acetate/dichloromethane), to give 5.6 g (77%) of a solid, m.p. 147°-151° C. The solid was recrystallized from methanol to give 3.14 g (43%) of 1-(1H-indol-7-ylcarbonyl)-4-[3(trifuoromethyl)phenyl]piperazine, m.p. 149°-151° C.

Workup

  1. concentrationThe solvent was then concentrated off
  2. customthe resulting oil was partitioned between ethyl acetate and water
  3. extractionThe aqueous was extracted twice with ethyl acetate
  4. washthe organics were washed with water
  5. dry with materialdried (saturatedNaCl, MgSO4)
  6. customThe desired amine was purified via flash chromatography (10% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-097ede3d7083493f8130555f069ae7b0
Source dataset
uspto-grants-1994_07
Patent number
US05330986

Reaction notes

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