Hydrochloric Acid → 1-(4-(methylsulfonyl)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-one hydrochloric acid

HRID 1518440Notes

Reaction equation

HRID 1518440 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[CH:13][C:12]2=[O:31])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[ClH:32]>>[ClH:32].[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:13][C:12]2=[O:31])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 25204174Tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 673669641-(4-(methylsulfonyl)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-one hydrochloric acid

Procedure

A mixture of tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (5.279 g, 11.77 mmol) and hydrogen chloride (37% in H2O, 40 mL, EMD) was stirred for 20 min and then concentrated in vacuo. The obtained solid was dissolved in methanol (80 mL) and diethyl ether (300 mL) was added. The resulting solid was filtered to give 4.52 g of the desired product as an off-white solid. MS (ESI) 349 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe obtained solid was dissolved in methanol (80 mL)
  3. additiondiethyl ether (300 mL) was added
  4. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-43e91ef4ca9f4958bd553cfea4a344ce
Source dataset
uspto-grants-2012_07
Patent number
US08232404B2

Reaction notes

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