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

HRID 1985503Notes

Reaction equation

HRID 1985503 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-0f3bc086795c44f7a21662b94d9e01f9
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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