Triethylamine → 1-(3-chlorobenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine

HRID 67075

Reaction equation

HRID 67075 reaction equation
Cl.[NH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:3]1=[O:18].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1)=[O:22].C(N(CC)CC)C>CO>[Cl:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[C:21]([CH2:20][N:15]1[CH2:14][CH2:13][CH:12]([N:4]2[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:2][C:3]2=[O:18])[CH2:17][CH2:16]1)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 387382-Bromo-3'-chloroacetophenoneHCID 183213553-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one hydrochloride

Product 1

HCID 127979921-(3-chlorobenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidineYield 50.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example, 2.67 g of 4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine mono-hydrochloride, 2.33 g of α-bromo-m-chloroacetophenone, 2.8 ml of triethylamine and 30 ml of methanol are mixed and stirred at room temperature overnight. Then, the white crystals deposited are separated by filtration, successively washed with methanol and water and dried to obtain 2.89 g of a crude product. The crude product is recrystallized from a mixed solvent of chloroform and ethanol to obtain 1.93 g of the desired product.

Workup

  1. customThen, the white crystals deposited are separated by filtration
  2. washsuccessively washed with methanol and water
  3. customdried
  4. customto obtain 2.89 g of a crude product
  5. customThe crude product is recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-1f54b4acf24a4bcbaa663e740ddf1acb
Source dataset
uspto-grants-1982_08
Patent number
US04344948

Linked notes

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