Piperazine → 2-Piperazin-1-yl-quinazoline

HRID 1276596Notes

Reaction equation

HRID 1276596 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C1(C)C=CC=CC=1>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[N:11][C:2]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 740542-Chloroquinazoline

Product 1

HCID 64232662-Piperazin-1-yl-quinazolineYield 104.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-chloroquinazoline (5 g) in 20 mL of toluene is added dropwise to a refluxing solution of piperazine (20 g) in 150 mL of toluene. The solution is heated for an additional 24 hours. After cooling to 0° C. for about 30 minutes, the solution is filtered. The filtrate is extracted with 10% acetic acid. The aqueous extracts are washed with ether, basified and extracted with toluene. The toluene layer is then washed with water, dried and concentrated. The resulting material is placed under vacuum overnight to afford the title compound (6.8 g, m.p. 64-66° C.). 1H NMR (CDCl3) 9.0 (s, 1H) , 7.66 (m, 2H), 7.56 (d, J=8 Hz, 1H), 7.22 (ddd, J=8,7,1 Hz, 1H), 4.0 (t, J=5 Hz, 4H), 3.05 (t, J=5 Hz, 4H).

Workup

  1. temperatureThe solution is heated for an additional 24 hours
  2. filtrationthe solution is filtered
  3. extractionThe filtrate is extracted with 10% acetic acid
  4. washThe aqueous extracts are washed with ether
  5. extractionextracted with toluene
  6. washThe toluene layer is then washed with water
  7. customdried
  8. concentrationconcentrated
  9. customis placed under vacuum overnight

Sources & evidence

ORD record
ord-ef54229253a44451904777eac1b9c5d5
Source dataset
uspto-grants-2000_12
Patent number
US06166205

Reaction notes

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