Benzyl Alcohol → HCID 9921566, compound

HRID 1357589Notes

Reaction equation

HRID 1357589 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.

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-5c94cf7ddc33424aac8559c801bfdde9
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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