Piperazine → HCID 10267995, compound

HRID 1296604Notes

Reaction equation

HRID 1296604 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4](Cl)[N:3]=1.[C:9]1([CH2:19][OH:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.[H-].[Na+].[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>O1CCOCC1.C(#N)C>[C:9]1([CH2:19][O:20][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[N:3]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 4837Piperazine2×HCID 209081-NaphthalenemethanolHCID 24758Sodium hydride2×HCID 785042,6-Dichloropyrazine

Product 1

HCID 10267995HCID 10267995, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,6-dichloropyrazine (298 mg, 2.00 mmol) and 1-naphthylmethanol (348 mg, 2.20 mmol) in dioxane (5 mL) was added NaH (55% in mineral oil, 96 mg, 2.2 mmol) at room temperature. The reaction was stirred at room temperature and monitored by GC. After 3 h, piperazine (189 mg, 2.20 mmol) and NaH (55% in oil, 96 mg, 2.2 mmol) was added into the reaction flask at room temperature. The reaction mixture was stirred at room temperature for 24 h. The solvent was evaporated off. To the residue was added piperazine (671 mg, 7.80 mmol) and acetonitrile (5 mL) and the solution was heated under reflux for 5 h. The reaction mixture was directly loaded on a short column of silica gel for flash column chromatography. Elution with MeOH/dichloromethane (1:9) furnished 0.41 g (64%) of the title compound. HRMS m/z calcd for C19H20N4O (M)+ 321.1715, found 321.1721. Anal. (C19H20N4O.0.1 H2O) C, H, N.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 24 h
  2. customThe solvent was evaporated off
  3. temperaturethe solution was heated
  4. temperatureunder reflux for 5 h
  5. washElution with MeOH/dichloromethane (1:9)

Sources & evidence

ORD record
ord-27ae7b14814140e8b5adbd0e4399a782
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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