2(1h)-Quinazolinone,3,4-dihydro-8-methoxy-3-[1-(phenylmethyl)-4-piperidinyl]- → 8-Methoxy-3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one

HRID 2250257Notes

Reaction equation

HRID 2250257 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:23][C:22]3[C:17](=[C:18]([O:24][CH3:25])[CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:26])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:25][O:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:17]=1[NH:16][C:15](=[O:26])[N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH2:23]2

Participants

4

Reactant 1

HCID 211021562(1h)-Quinazolinone,3,4-dihydro-8-methoxy-3-[1-(phenylmethyl)-4-piperidinyl]-

Product 1

HCID 183210478-Methoxy-3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-oneYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(1-Benzyl-piperidin-4-yl)-8-methoxy-3,4-dihydro-1H-quinazolin-2-one (100 mg, 0.28 mmol) in methanol (5 mL) was flushed with nitrogen, and treated with palladium on charcoal (10%, 10 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Column chromatography gave 68 mg (93%) of the desired material. LC/MS: tR=1.11 min, 262.23 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1b4a5ad1d8ea44599dc06ff86c11de49
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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