Triethylamine → HCID 67582908, compound

HRID 1416482Notes

Reaction equation

HRID 1416482 reaction equation
[CH2:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:6]=1)[CH:2]=[CH2:3].C(N(CC)CC)C.[C:28](Cl)(=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:30]([O:29][C:28]([N:18]1[CH2:17][CH2:16][N:15]([C:7]2[N:6]=[C:5]([O:4][CH2:1][CH:2]=[CH2:3])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH2:20][CH2:19]1)=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 54172249HCID 54172249, compound

Product 1

HCID 67582908HCID 67582908, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[(2-propen-1-yl)oxy]-2-(1-piperazinyl)quinazoline (1.80 g) in dry methylene chloride (18 ml) is added triethylamine (1.88 ml) with stirring under ice-cooling, and thereto is further added dropwise a solution of benzyl chlorocarbonate (1.04 ml) in dry methylene chloride (3 ml). The mixture is stirred under ice-cooling for 2 hours. The reaction mixture is diluted with chloroform, washed with diluted hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The solution is evaporated to dryness under reduced pressure, and the residue is purified by medium pressure liquid column chromatography (eluent, chloroform) to give 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(2-propen-1-yl)oxy]quinazoline (1.76 g) as crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred under ice-
  3. temperaturecooling for 2 hours
  4. washwashed with diluted hydrochloric acid and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solution is evaporated to dryness under reduced pressure
  7. customthe residue is purified by medium pressure liquid column chromatography (eluent, chloroform)

Sources & evidence

ORD record
ord-81a834da98374cbe971bf7e72593c33c
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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