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 1177778Notes

Reaction equation

HRID 1177778 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-6027645617da4b7e9c2cf0fd5e1f844b
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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