3-(1-benzylpiperidin-4-yl)-4-(4-chlorophenyl)-3,4-dihydro-2(1H)-quinazolinone → 3-(piperidin-4-yl)-4-(4-chlorophenyl)-3,4-dihydro-2(1H)-quinazolinone

HRID 479466Notes

Reaction equation

HRID 479466 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:23]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:31])[CH2:10][CH2:9]1)C1C=CC=CC=1>C(Cl)Cl.ClC(OC(Cl)C)=O>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:23]([C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:31])[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 121093893-(1-benzylpiperidin-4-yl)-4-(4-chlorophenyl)-3,4-dihydro-2(1H)-quinazolinone

Product 1

HCID 187708913-(piperidin-4-yl)-4-(4-chlorophenyl)-3,4-dihydro-2(1H)-quinazolinoneYield 97.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 5213051-Chloroethyl chloroformateSolvent

Procedure

To a solution of 1.40 g (3.25 mmol) of 3-(1-benzylpiperidin-4-yl)-4-(4-chlorophenyl)-3,4-dihydro-2(1H)-quinazolinone in methylene chloride, α-chloroethyl chloroformate was added dropwise under ice-cooling and stirred for one hour. After concentration under reduced pressure, the residue was dissolved with 28 ml of methanol and stirred at room temperature for 2 hours and under ice-cooling for one hour. The precipitated crystals were collected to give 1.08 g (3.16 mmol) of the title compound as colorless crystal.

Workup

  1. temperaturecooling
  2. concentrationAfter concentration under reduced pressure
  3. dissolutionthe residue was dissolved with 28 ml of methanol
  4. stirringstirred at room temperature for 2 hours and under ice-
  5. temperaturecooling for one hour
  6. customThe precipitated crystals were collected

Sources & evidence

ORD record
ord-e991532bd08849448ed1659524cad056
Source dataset
uspto-grants-2003_11
Patent number
US06645971B1

Reaction notes

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