Urea → HCID 178480235, compound

HRID 406831Notes

Reaction equation

HRID 406831 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)=O.[NH2:17][C:18](N)=[O:19].[OH-].[Na+]>C(O)(=O)C>[CH3:16][N:13]1[CH2:14][CH2:15][CH:10]([C:8]2[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[NH:1][C:18](=[O:19])[N:17]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 1176UreaHCID 14798Sodium HydroxideHCID 21414385(2-Aminophenyl)(1-methylpiperidin-4-yl)methanone

Product 1

HCID 178480235HCID 178480235, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of (2-aminophenyl)(1-methylpiperidin-4-yl)methanone (1.10 g, 4.58 mmol), urea (550 mg, 9.17 mmol) and acetic acid (15 mL) was heated to overnight. The mixture was cooled to rt, neutralized with 1 N sodium hydroxide and concentrated to ˜10 mL on a rotary evaporator. The aqueous residue was extracted with ethyl acetate and the combined organics were dried over sodium sulfate, filtered and concentrated on a rotary evaporator to afford 4-(1-methylpiperidin-4-yl)quinazolin-2(1H)-one as a yellow solid (1.10 g, 97%).

Workup

  1. temperaturewas heated to overnight
  2. concentrationconcentrated to ˜10 mL on a rotary evaporator
  3. extractionThe aqueous residue was extracted with ethyl acetate
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-977e3508c3e3465895d2d8034a8654d9
Source dataset
uspto-grants-2014_06
Patent number
US08754092B2

Reaction notes

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