Benzyl Alcohol → HCID 9921566, compound

HRID 1296627Notes

Reaction equation

HRID 1296627 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[N:4][CH:3]=1.[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:21][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[N:7]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 244Benzyl AlcoholHCID 1079922-Chloro-6-(1-piperazinyl)pyrazine

Product 1

HCID 9921566HCID 9921566, compoundYield 90.5%

Conditions

Temperature
125 °C

Procedure

A mixture of the product from example 13, step 2 (0.73 g, 3.68 mmol), benzyl alcohol (9.4 g, 87 mmol) and K-t-BuO was stirred at 125° C. for 4.5 h. The reaction mixture was purified by silica gel chromatography (13×5 cm) using CHCl3/MeOH (7:3 followed by 9:1) as eluent. Solvents were evaporated off and the residue was redissolved in ethyl acetate. Filtration and concentration in vacuo furnished 0.90 g (90%) of the title compound as a beige oil. HRMS m/z calcd for C15H18N4O (M)+ 270.1481, found 270.1482. Anal. (C15H18N4O) C, H, N. *This compound was also characterized as its maleate salt: mp 155-156° C. HRMS m/z calcd for C15H18N4O (M)+ 270.1481, found 270.1482. Anal. (C15H18N4O.C4H4O4) C, H, N.

Workup

  1. customThe reaction mixture was purified by silica gel chromatography (13×5 cm)
  2. customSolvents were evaporated off
  3. dissolutionthe residue was redissolved in ethyl acetate
  4. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-1b03822e60fa4e13a188da2b9f184905
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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