Hydrochloric Acid → 3,4-dihydro-1-(4-piperidinyl)-2(1H)-Quinazolinone

HRID 67084Notes

Reaction equation

HRID 67084 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:23]3[C:18]([CH2:19][CH:20]=[CH:21][CH:22]=3)=[CH:17][NH:16][C:15]2=[O:24])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl.O.[H][H]>[Pd].CO>[N:14]1([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][NH:16][C:15]1=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 205282081-benzyl-4-[3,5-dihydro-2(1H)-quinazolinon-1-yl]-piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 130510263,4-dihydro-1-(4-piperidinyl)-2(1H)-QuinazolinoneYield 44.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

In this reference example, 16.0 g of 1-benzyl-4-[3,5-dihydro-2(1H)-quinazolinon-1-yl]-piperidine, 4.0 g of 10% Pd-C, 50 ml of 1 N hydrochloric acid, 150 ml of water and 300 ml of methanol are mixed and stirred at 40° C. Hydrogen gas is introduced to the mixture for 5 hours with stirring. Then, the Pd-C is removed by filtration and the filtrate is concentrated. The white crystalline residue is dissolved in 50 ml of water. The solution is adjusted to pH 10 with aqueous 5 N sodium hydroxide and extracted with chloroform. The extract is washed with water, dried and thereafter concentrated. Then, 50 ml of a mixture of ethyl acetate and n-hexane (1:1 by volume) is added to the residue. After trituration, the solid is separated by filtration, washed with the same mixed solvent to obtain 9.9 g of a crude product. The crude product is recrystallized from water-ethanol to obtain 5.1 g of the desired product.

Workup

  1. stirringwith stirring
  2. customThen, the Pd-C is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. dissolutionThe white crystalline residue is dissolved in 50 ml of water
  5. extractionextracted with chloroform
  6. washThe extract is washed with water
  7. customdried
  8. concentrationconcentrated
  9. additionThen, 50 ml of a mixture of ethyl acetate and n-hexane (1:1 by volume) is added to the residue
  10. customAfter trituration, the solid is separated by filtration
  11. washwashed with the same mixed solvent
  12. customto obtain 9.9 g of a crude product
  13. customThe crude product is recrystallized from water-ethanol

Sources & evidence

ORD record
ord-3dd9b2d36e314ee4a46ae1d5be5ced82
Source dataset
uspto-grants-1982_08
Patent number
US04344948

Reaction notes

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