Dichloromethane → tert-Butyl 4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carboxylate

HRID 1172285Notes

Reaction equation

HRID 1172285 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[CH2:6][NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)([O-])=O.C1N=CN([C:30](N2C=NC=C2)=[O:31])C=1.C(Cl)Cl.CCOC(C)=O>C1COCC1>[O:31]=[C:30]1[N:7]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:6][C:5]2[C:4](=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:1]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 13046886tert-Butyl 4-{[(2-nitrophenyl)methyl]amino}piperidine-1-carboxylate

Product 1

HCID 53415303tert-Butyl 4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carboxylateYield 24.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 4-(2-nitrobenzylamino)piperidine-1-carboxylate (13.2 g, 43.2 mmol) in THF (400 ml) was added a solution of CDI (7.7 g, 47.5 mmol) in 1:1 DCM: THF (100 ml) dropwise over 1 hour followed by stirring the reaction mixture for a further 16 hours. The reaction mixture was evaporated to give an oil that, when treated with EtOAc, precipitated the desired product. The precipitate was washed with cold EtOAc and dried to give a yellow solid (3.5 g). LC/MS (10% to 99%): M/Z (M+H)+ (obs)=332; tR=3.01.

Workup

  1. customThe reaction mixture was evaporated
  2. customto give an oil that, when
  3. customprecipitated the desired product
  4. washThe precipitate was washed with cold EtOAc
  5. customdried

Sources & evidence

ORD record
ord-09d3c9277dbd4306b846f92f6906310a
Source dataset
uspto-grants-2010_11
Patent number
US07834000B2

Reaction notes

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