Hydrochloric Acid → 3-(Piperidin-4-yl)-1,8-naphthyridin-2(1H)-one dihydrochloride

HRID 132354Notes

Reaction equation

HRID 132354 reaction equation
[ClH:1].O[CH:3]([C:22]1[C:23]([NH:28][C:29](=[O:34])C(C)(C)C)=[N:24][CH:25]=[CH:26][CH:27]=1)[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>[ClH:1].[ClH:1].[NH:12]1[CH2:11][CH2:10][CH:9]([C:4]2[C:29](=[O:34])[NH:28][C:23]3[C:22]([CH:3]=2)=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59731884tert-Butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(2-pivalamidopyridin-3-yl)propan-2-yl)piperidine-1-carboxylate

Product 1

HCID 673180313-(Piperidin-4-yl)-1,8-naphthyridin-2(1H)-one dihydrochlorideYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (25 mL, 305 mmol) was added with stirring to a mixture of tert-butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(2-pivalamidopyridin-3-yl)propan-2-yl)piperidine-1-carboxylate (14.0 g, 30.2 mmol) and water (75 mL). Reaction was heated to reflux and held for 25 hours. Mixture was concentrated in vacuo. Residue was crystallized from ethanol. Title compound was obtained as white solid in 33% yield. (M+H)+=230.2.

Workup

  1. customReaction
  2. temperaturewas heated
  3. temperatureto reflux
  4. concentrationMixture was concentrated in vacuo
  5. customResidue was crystallized from ethanol

Sources & evidence

ORD record
ord-7d39bc2a538a415faae6b68bd2dd2376
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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