Hydrochloric Acid → 4-(4-fluorobenzyloxy)-1-[4-(2-aminoethoxy)phenyl]-1H-pyridin-2-one

HRID 15069Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1.[F:25][C:26]1[CH:52]=[CH:51][C:29]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][N:35]([C:38]3[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH2:46][N:47]=[N+]=[N-])=[CH:40][CH:39]=3)[C:34](=[O:50])[CH:33]=2)=[CH:28][CH:27]=1.Cl>O>[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][N:35]([C:38]3[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH2:46][NH2:47])=[CH:40][CH:39]=3)[C:34](=[O:50])[CH:33]=2)=[CH:51][CH:52]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Triphenylphosphine (50 mg) was added to THF (5 mL)-water (1 mL) solution of 4-(4-fluorobenzyloxy)-1-[4-(2-azidoethoxy)phenyl]-1H-pyridin-2-one (50 mg), and stirred at 80° C. for 2 hours. Allowing the reaction liquid to cool off, 1N hydrochloric acid was added, followed by washing with diethyl ether. The aqueous layer was rendered basic by addition of 1N aqueous sodium hydroxide, extracted with chloroform and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was reprecipitated from diethyl ether-hexane to provide the title compound (9.8 mg, 21%).

Workup

customAllowing the reaction liquid
temperatureto cool off
washby washing with diethyl ether
additionThe aqueous layer was rendered basic by addition of 1N aqueous sodium hydroxide
extractionextracted with chloroform
dry with materialdried over anhydrous magnesium sulfate
concentrationConcentrating the solvent under reduced pressure
customthe residue was reprecipitated from diethyl ether-hexane

Sources & evidence

ORD record: ord-42e0365d7d584ab28bbbe9e1beb4e27c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732456B2

Reaction notes

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