Hydrochloric Acid → 6-(4-Piperidinyl)-4H-benzo[1,4]oxazin-3-one

HRID 495422

Reaction equation

HRID 495422 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[CH:9][C:10]3[O:15][CH2:14][C:13](=[O:16])[NH:12][C:11]=3[CH:17]=2)=[CH:3][CH:2]=1.Cl>CO.CCOCC.[Pt](=O)=O>[NH:1]1[CH2:2][CH2:3][CH:4]([C:7]2[CH:8]=[CH:9][C:10]3[O:15][CH2:14][C:13](=[O:16])[NH:12][C:11]=3[CH:17]=2)[CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 223266866-(4-Pyridyl)-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 223267216-(4-Piperidinyl)-4H-benzo[1,4]oxazin-3-oneYield 100.8%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 6-(4-pyridyl)-4H-benzo[1,4]oxazin-3-one (0.57 g, 2.52 mmol), in methanol (15 mL) was treated with platinum (IV) oxide (50 mg, 0.22 mmol) and 1M HCl in ether (2.7 mL) and stirred at room temperature under an atmosphere of hydrogen for 24 h. The reaction mixture was filtered through celite and the filtrate evaporated in vacuo to give the title compound (0.59 g, 87%) as a pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-aab42d12505d4aff9039aae1fb862f60
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Linked notes

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