Piperazine → HCID 22482014, compound

HRID 1296645Notes

Reaction equation

HRID 1296645 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:13]1[CH:18]=[N:17][CH:16]=[C:15](Cl)[N:14]=1.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][C:13]2[CH:18]=[N:17][CH:16]=[C:15]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:14]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 680224-Fluorobenzylic alcoholHCID 785042,6-Dichloropyrazine

Product 1

HCID 22482014HCID 22482014, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Fluorobenzyl alcohol (0.189 g, 1.50 mmol) was dissolved in THF (1 mL) and treated with NaH (0.065 g, 55% dispersion in mineral oil, 1.5 mmol). The reaction mixture was stirred at room temperature for 3 h. A solution of 2,6-dichloropyrazine (1.57 g, 10.5 mmol) in THF (7 mL) was added and the resulting mixture was stirred for 4 h at room temperature. Piperazine (0.580 g, 6.75 mmol) and K2CO3 (0.43 g, 4.5 mmol) were added and the mixture was stired at 60° C. over night. Filtration, concentration, and purification by chromatography on silica gel using ethyl acetate/acetic acid/methanol/water (24:3:3:2) as eluent furnished 0.20 g (46%) of the title compound as a white solid: mp 183° C. HRMS m/z calcd for C15H17FN4O (M)+ 288.1386, found 288.1380. Anal. (C15H17FN4O.2.6H2O) C, H, N.

Workup

  1. stirringthe resulting mixture was stirred for 4 h at room temperature
  2. waitthe mixture was stired at 60° C. over night
  3. filtrationFiltration, concentration, and purification by chromatography on silica gel

Sources & evidence

ORD record
ord-1a52a3839283486180791b16b0a281af
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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