Hydrochloric Acid → 3-(piperidin-4-yl)-1,6-naphthyridin-2(1H)-one

HRID 1985505

Reaction equation

HRID 1985505 reaction equation
Cl.O[CH:3]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:27]=1[NH:28][C:29](=[O:34])C(C)(C)C)[CH:4]([CH:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)C(OC)=O>O>[NH:12]1[CH2:11][CH2:10][CH:9]([C:4]2[C:29](=[O:34])[NH:28][C:27]3[C:22]([CH:3]=2)=[CH:23][N:24]=[CH:25][CH:26]=3)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59732007tert-Butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(4-pivalamidopyridin-3-yl)propan-2-yl)piperidine-1-carboxylate

Product 1

HCID 597319443-(piperidin-4-yl)-1,6-naphthyridin-2(1H)-oneYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (8.0 mL, 97 mmol) was added with stirring to a mixture of tert-butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(4-pivalamidopyridin-3-yl)propan-2-yl)piperidine-1-carboxylate (1.2 g, 2.6 mmol) and water (24 mL). Reaction was heated to reflux and held for 14 hours. Mixture was concentrated in vacuo. Residue was treated with acetonitrile (70 mL) and then concentrated in vacuo. Residue was crystallized from ethanol. Title compound was obtained as white solid in 77% yield. (M+H)+=230.1.

Workup

  1. customReaction
  2. temperaturewas heated
  3. temperatureto reflux
  4. concentrationMixture was concentrated in vacuo
  5. additionResidue was treated with acetonitrile (70 mL)
  6. concentrationconcentrated in vacuo
  7. customResidue was crystallized from ethanol

Sources & evidence

ORD record
ord-46faefac5a894d8892bb4ce26a2a1e56
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Linked notes

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