Triethylamine → HCID 67582811, compound

HRID 1416495Notes

Reaction equation

HRID 1416495 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:7]=1)[CH2:2][CH:3]=[CH2:4].C(N(CC)CC)C.[C:29](Cl)(=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:31]([O:30][C:29]([N:19]1[CH2:20][CH2:21][N:16]([C:8]2[N:7]=[C:6]([O:5][CH2:1][CH2:2][CH:3]=[CH2:4])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH2:17][CH2:18]1)=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 541306714-[(But-3-en-1-yl)oxy]-2-(piperazin-1-yl)quinazoline

Product 1

HCID 67582811HCID 67582811, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[(3-buten-1-yl)oxy]-2-(1-piperazinyl)quinazoline (23.3 g) in dry methylene chloride (200 ml) is added triethylamine (22.9 ml) with stirring under ice-cooling, and thereto is further added dropwise a solution of benzyl chlorocarbonate (12.3 ml) in dry methylene chloride (30 ml). The mixture is stirred under ice-cooling for 5 hours. The reaction mixture is diluted with chloroform, washed with 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-[(3-buten-1-yl)oxy]quinazoline (26.7 g) as crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred under ice-
  3. temperaturecooling for 5 hours
  4. washwashed with 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-c1be9a2b6aeb4ecb87e6248efe1ad962
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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