3-(1-Benzylpiperidin-4-yl)-8-fluoro-3,4-dihydroquinazolin-2(1H)-one → 2(1h)-Quinazolinone,8-fluoro-3,4-dihydro-3-(4-piperidinyl)-

HRID 2099732Notes

Reaction equation

HRID 2099732 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:23][C:22]3[C:17](=[C:18]([F:24])[CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:25])[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].CO>[F:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:17]=1[NH:16][C:15](=[O:25])[N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH2:23]2

Participants

4

Reactant 1

HCID 211021543-(1-Benzylpiperidin-4-yl)-8-fluoro-3,4-dihydroquinazolin-2(1H)-one

Product 1

HCID 211022172(1h)-Quinazolinone,8-fluoro-3,4-dihydro-3-(4-piperidinyl)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 250 mL flask was charged with 3-(1-benzylpiperidin-4-yl)-8-fluoro-3,4-dihydroquinazolin-2(1H)-one (1.40 g, 4.12 mmol) and methanol (25.0 mL). The suspension was heated with a heat gun to aid in dissolution. The flask was flushed with nitrogen, treated with palladium on charcoal (141 mg, 0.032 equiv), flushed with nitrogen, then hydrogen, and vigorously stirred under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated to give 0.99 g (97%) as a white solid which was used without purification. 1H-NMR (CDCl3, 500 MHz) δ 1.71 (m, 4H), 2.75 (m, 2H), 3.16 (m, 2H), 4.38 (s, 2H), 4.46 (m, 1H), 6.77 (bs, 1H), 6.81-6.89 (m, 2H), 6.95 (m, 1H). Mass spec.: 250.22 (MH)+.

Workup

  1. temperatureThe suspension was heated with a heat gun
  2. dissolutionto aid in dissolution
  3. customThe flask was flushed with nitrogen
  4. customflushed with nitrogen
  5. customThe reaction was flushed with nitrogen
  6. filtrationfiltered through celite
  7. concentrationconcentrated
  8. customto give 0.99 g (97%) as a white solid which
  9. customwas used without purification

Sources & evidence

ORD record
ord-5a12ef1e3e20416593cf4cc9afdcf153
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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