Dimethylformamide → HCID 19767631, compound

HRID 1590654Notes

Reaction equation

HRID 1590654 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=C[CH:6]=[N:7]2.[C:12]([O:16][K])(C)([CH3:14])[CH3:13].C(C1OC1)Cl.C[N:24](C=O)C>>[O:16]1[CH2:14][CH:12]1[CH2:13][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[N:24][CH:6]=[N:7]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7835EpichlorohydrinHCID 135441757Quinolin-5-olHCID 178418922HCID 178418922, compound

Product 1

HCID 19767631HCID 19767631, compound

Conditions

Temperature
50 °C

Procedure

In 30 ml of dried DMF was dissolved 2 g of 5-hydroxyquinoline, and 1.5 g of t-butoxypotassium was added thereto, followed by heating and stirring at 50° C. for 1 hour. To the reaction liquid was added 4 g of epichlorohydrin, and the liquid was then heated with stirring at 90° C. for 3 hours. The solvent was distilled off under reduced pressure, and the resultant residue was then purified by the use of a silica gel column chromatograph. On allowing an effluent solvent of chloroform:methanol=100:1 to flow therethrough, 5-(2,3-epoxypropoxy)quinazoline was obtained in an oily state in an amount of 0.84 g. In 20 ml of ethanol were dissolved 0.84 g of this epoxy compound and 1.05 g of N-diphenylmethylpiperazine, and the liquid was then heated under reflux for 3 hours. After the reaction, the solvent was distilled off, and the resultant residue was then purified through the silica gel column chromatograph. On allowing the effluent solvent of chloroform:methanol=50:1 to flow therethrough, the intended product 5-[3-(4-diphenylmethylpiperazine-1-yl)-2-hydroxypropoxy]quinazoline was obtained in a powdery state in an amount of 0.48 g.

Workup

  1. additionwas added
  2. temperatureby heating
  3. customTo the reaction liquid
  4. temperaturethe liquid was then heated
  5. stirringwith stirring at 90° C. for 3 hours
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resultant residue was then purified by the use of a silica gel column chromatograph

Sources & evidence

ORD record
ord-140ee56678dd401894c39313a54d9adb
Source dataset
uspto-grants-1993_04
Patent number
US05204348

Reaction notes

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