Ammonium Hydroxide → 3,4-dihydro-1-(4-piperidinyl)-2(1H)-Quinazolinone

HRID 1377674Notes

Reaction equation

HRID 1377674 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][NH:16][C:15]2=[O:24])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.[NH4+].[OH-]>ClC(Cl)C.CO>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][NH:16][C:15]2=[O:24])[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 5213051-Chloroethyl chloroformateHCID 130510251-(1-benzyl-4-piperidinyl)-3,4-dihydroquinazolin-2(1H)-one

Product 1

HCID 130510263,4-dihydro-1-(4-piperidinyl)-2(1H)-Quinazolinone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1-(1-benzyl-4-piperidinyl)-3,4-dihydroquinazolin-2(1H)-one (947 g, 295 mmol) from Step 4 in dry dichloroethane (20 mL) was added 1-chloroethyl chloroformate (0.35 mL, 3.2 mmol). The reaction was refluxed for 3 h. The solvent was rmoved under reduced pressure and the residue was dissolved in MeOH (50 mL) and the solution was refluxed for 1 h. The reaction was cooled to ambient temperature, conc. NH4OH (1 mL) was added, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 90:10:1 CHCl3 :MeOH:NH4OH as eluant. 1-(4-Piperidinyl)-3,4-dihydroquinazolin-2(1H)-one was obtained as an oil (48% yield).

Workup

  1. temperatureThe reaction was refluxed for 3 h
  2. temperaturethe solution was refluxed for 1 h
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-d99d5b2e03424d5089da19123c51a9c7
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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