Phosgene → 6-Piperidin-1-yl-1H-quinazoline-2,4-dione

HRID 855642Notes

Reaction equation

HRID 855642 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:17](Cl)(Cl)=[O:18]>O1CCOCC1>[N:11]1([C:8]2[CH:7]=[C:3]3[C:2](=[CH:10][CH:9]=2)[NH:1][C:17](=[O:18])[NH:6][C:4]3=[O:5])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 107276062-Amino-5-(piperidin-1-yl)benzamide

Product 1

HCID 134217986-Piperidin-1-yl-1H-quinazoline-2,4-dioneYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Amino-5-piperidin-1-yl-benzamide (210 mg, 2.33 mmol) in dry dioxane (50 mL) was treated with 2N phosgene solution (1.28 mL in toluene). The resulting orange precipitate was heated to 80 C to give after 3 h, a pale yellow solid. The solution was cooled in an ice bath and the product was collect by filtration to give 6-Piperidin-1-yl-1H-quinazoline-2,4-dione 525 mg (91% yield) HPLC tr=3.6 min (85%), LCMS m/e 246.2 (M+H).

Workup

  1. temperatureThe resulting orange precipitate was heated to 80 C
  2. customto give after 3 h
  3. temperatureThe solution was cooled in an ice bath
  4. filtrationthe product was collect by filtration

Sources & evidence

ORD record
ord-16635085e7c24878bca954cb8c40857d
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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