Hydrochloric Acid → 8-Fluoro-3-(piperidin-4-yl)quinolin-2(1H)-one hydrochloride

HRID 501984Notes

Reaction equation

HRID 501984 reaction equation
[F:1][C:2]1[C:3]([NH:28][C:29](=[O:34])C(C)(C)C)=[C:4]([CH:8](O)[CH:9]([CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)C(OC)=O)[CH:5]=[CH:6][CH:7]=1.O.[ClH:36]>CO>[ClH:36].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:28][C:29](=[O:34])[C:9]([CH:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1)=[CH:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59424341tert-Butyl 4-(1-(3-fluoro-2-pivalamidophenyl)-1-hydroxy-3-methoxy-3-oxopropan-2-yl)piperidine-1-carboxylate

Product 1

HCID 673189488-Fluoro-3-(piperidin-4-yl)quinolin-2(1H)-one hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-(1-(3-fluoro-2-pivalamidophenyl)-1-hydroxy-3-methoxy-3-oxopropan-2-yl)piperidine-1-carboxylate (7.86 g, 16.4 mmol) was dissolved in methanol (20 mL). Water (45 mL) was added to the mixture followed by concentrated hydrochloric acid (15 mL, 183 mmol). The reaction was heated to reflux and held for 2.5 h. The reaction mixture was concentrated in vacuo, redissolved in ethanol (50 mL), and concentrated in vacuo. The residue was crystallized from ethanol. The resulting solids were filtered, washed with cold ethanol, and dried in vacuo. The title compound was obtained as white solid in 83% yield. 1H NMR (500 MHz, DMSO-d6): δ 11.85 (s, 1H), 8.98 (m, 1H), 8.85 (m, 1H), 7.75 (s, 1H), 7.54 (d, J=7.63, 1H), 7.36 (dd, J=0.22, 8.09, 1H), 7.21-7.11 (m, 1H), 3.41-3.29 (m, 2H), 3.14-2.94 (m, 3H), 2.02 (d, J=13.43, 2H), 1.88-1.71 (m, 2H). Mass spec.: 247.2 (MH)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionredissolved in ethanol (50 mL)
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from ethanol
  7. filtrationThe resulting solids were filtered
  8. washwashed with cold ethanol
  9. customdried in vacuo

Sources & evidence

ORD record
ord-28267e04e9674d3792b714cb2eadc34e
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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