Hydrochloric Acid → 2-[3-{2-[4-(4Fluorobenzoyl)-1-piperidinyl]ethyl}-2,4-dioxo-3,4-dihydro-1(2H)-quinazolinyl]-N,N-dimethylacetamide hydrochloride

HRID 1059019

Reaction equation

HRID 1059019 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][C:17]3=[O:27])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[Cl:32][CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35].Cl>CN(C=O)C.O>[ClH:32].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]([CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[C:17]3=[O:27])[CH2:10][CH2:9]2)=[O:7])=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3822KetanserinHCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamide

Product 1

HCID 223224082-[3-{2-[4-(4Fluorobenzoyl)-1-piperidinyl]ethyl}-2,4-dioxo-3,4-dihydro-1(2H)-quinazolinyl]-N,N-dimethylacetamide hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-{2-[4-(4-Fluorobenzoyl)-1-piperidinyl]ethyl}-2,4(1H,3H)-quinazolinedione was dissolved in DMF (5 ml) and NaH (60% dispersion in mineral oil) added. After 0.5 hours, 2-chloro-N,N-dimethylacetamide was added and the solution stirred at room temperature for 16 hours. Water and ethyl actetate were added, the organic phase separated, dried and concentrated to an oil. Purification by chromatography (dichloromethane:methanol 95:5) gave an oil which was treated with 1.0 M ethereal hydrogen chloride solution to give the titled product as a solid(0.015 g).

Workup

  1. customthe organic phase separated
  2. customdried
  3. concentrationconcentrated to an oil
  4. customPurification by chromatography (dichloromethane:methanol 95:5)
  5. customgave an oil which

Sources & evidence

ORD record
ord-886038107c344552a94facccec33c4ac
Source dataset
uspto-grants-2003_02
Patent number
US06518286B1

Linked notes

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