Dimethylformamide → 1-(1-benzyl-4-piperidinyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 1377673Notes

Reaction equation

HRID 1377673 reaction equation
ClC(O[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)=O.[CH3:14][CH2:15][N:16]([CH:20]([CH3:22])C)[CH:17]([CH3:19])C.[CH3:23][N:24]([CH:26]=[O:27])[CH3:25]>>[CH2:20]([N:16]1[CH2:15][CH2:14][CH:23]([N:24]2[C:25]3[C:9](=[CH:10][CH:5]=[CH:6][CH:7]=3)[CH2:8][NH:11][C:26]2=[O:27])[CH2:19][CH2:17]1)[C:22]1[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 130510251-(1-benzyl-4-piperidinyl)-3,4-dihydroquinazolin-2(1H)-oneYield 50%

Procedure

To a solution of 1-benzyl-4-((2-aminomethyl)phenylamino)piperidine (1.74 g, 5.90 mmol) from Step 3 in dry DMF (50 mL) was added 4-nitrophenyl chloroformate (1.25 g, 6.20 mmol) and DIEA (3.08 mL, 17.7 mmol). After the reaction had been stirred at ambient temperature for 24 h, the solvent was removed under reduced pressure. The residue was dissolved in DCM (100 mL) and washed with saturated aqueous NaHCO3 (4×50 mL), dried (MgSO4), and filtered. The solution was concetrated and the precipitate which formed was collected by filtration to give 1-(1-benzyl-4-piperidinyl)-3,4-dihydroquinazolin-2(1H)-one as a white solid (50% yield).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in DCM (100 mL)
  3. washwashed with saturated aqueous NaHCO3 (4×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe precipitate which formed
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-eb61e40d86834d1d884451a3c77ed933
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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