Cyclopropylamine → 2-[1-(cyclopropylamino)ethyl]quinazolin-4(3H)-one

HRID 922461Notes

Reaction equation

HRID 922461 reaction equation
Br[CH:2]([C:4]1[NH:13][C:12](=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:3].[CH:15]1([NH2:18])[CH2:17][CH2:16]1>CN(C)C=O.O>[CH:15]1([NH:18][CH:2]([C:4]2[NH:13][C:12](=[O:14])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH3:3])[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 1355033222-(1-bromoethyl)-4(3H)-quinazolinone

Product 1

HCID 1363380882-[1-(cyclopropylamino)ethyl]quinazolin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 2-(1-bromoethyl)quinazolin-4(3H)-one (2.53 g) in N,N-dimethylformamide (30 mL) was added cyclopropylamine (3.46 mL), and the mixture was diluted with N,N-dimethylformamide (20 mL) and water (1 mL), and then stirred for 18 hours. The reaction solution was concentrated under reduced pressure, and to the residue was added aqueous sodium hydrogen carbonate solution, and then the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was triturated with diisopropyl ether/ethyl acetate (20:1) to give 2-[1-(cyclopropylamino)ethyl]quinazolin-4(3H)-one [REx(33-1)] (1.71 g) as a colorless powder.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue was added aqueous sodium hydrogen carbonate solution
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was triturated with diisopropyl ether/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-988668bb971d427b8135fdb0b24331ca
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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