1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 14390218, compound

HRID 2351645Notes

Reaction equation

HRID 2351645 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:33][C:34]([F:48])([F:47])[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([N:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[CH:36]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18](=[O:20])[N:44]3[CH2:43][CH2:42][N:41]([C:37]4[CH:38]=[CH:39][CH:40]=[C:35]([C:34]([F:47])([F:48])[F:33])[CH:36]=4)[CH2:46][CH2:45]3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390218HCID 14390218, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.0 g, 0.014 mole), 1,1'-carbonyldiimidazole (2.3 g, 0.014 mole), and anhydrous tetrahydrofuran (100 ml) was stirred at room temperature with a stream of nitrogen bubbling through the mixture for 21/2 hrs. A solution of N-(α, α, α-trifluoro-m-tolyl)-piperazine (3.2 g, 0.014 mole) in dry tetrahydrofuran (10 ml) was added and the reaction mixture was stirred at room temperature for 41/2 hrs. The tetrahydrofuran was evaporated and the residue dissolved was extracted with 5% potassium hydroxide solution (2×30 ml), water (30 ml), brine (25 ml), dried over sodium sulfate, and concentrated in vacuo. The residue (6.6 g) was twice recrystallized from isopropyl alcohol-isopropyl ether to give 3.3 g (47%) of white needles, mp 185°-186.5° C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 41/2 hrs
  2. customThe tetrahydrofuran was evaporated
  3. dissolutionthe residue dissolved
  4. extractionwas extracted with 5% potassium hydroxide solution (2×30 ml), water (30 ml), brine (25 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue (6.6 g) was twice recrystallized from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-0336ed447bcd47d28e8e560a2e483d9f
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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