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Bromomethyl 4-methoxyphenyl ketone → 1-(4-Methoxybenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine

HRID 67077
Notes
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Reaction equation

HRID 67077 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][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:22].C(N(CC)CC)C>CO>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([C:21]([CH2:20][N:15]2[CH2:14][CH2:13][CH:12]([N:4]3[CH2:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:2][C:3]3=[O:18])[CH2:17][CH2:16]2)=[O:22])=[CH:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 8471TriethylamineHCID 183213553-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one hydrochloride

Product 1

HCID 127979941-(4-Methoxybenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidineYield 66.9%

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Procedure

In this example, 4.00 g 4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine mono-hydrochloride, 3.44 g of α-bromo-p-methoxyacetophenone, 4.2 ml of triethylamine and 60 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 4.71 g of a crude product. The crude product is recrystallized from a mixed solvent of chloroform and ethanol to obtain 3.79 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 4.71 g of a crude product
  5. customThe crude product is recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-f4621af9c86c4805874ebad425ce9df9
Source dataset
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04344948

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes