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

HRID 1172362Notes

Reaction equation

HRID 1172362 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 (16.4 mmol, 7.86 g) was dissolved in methanol (20 mL). Water (45 mL) was added to the mixture followed by concentrated hydrochloric acid (183 mmol, 15 mL). Reaction was heated to reflux and held for 2.5 hours. Reaction mixture was concentrated in vacuo. Residue was dissolved in ethanol (50 mL) then concentrated in vacuo. Residue was crystallized from ethanol. Solids were filtered off, washed with cold ethanol then dried in vacuo. 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, J1=10.22, J2=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). MS m/e (M+H)+=247.2.

Workup

  1. customReaction
  2. temperaturewas heated
  3. temperatureto reflux
  4. customReaction mixture
  5. concentrationwas concentrated in vacuo
  6. dissolutionResidue was dissolved in ethanol (50 mL)
  7. concentrationthen concentrated in vacuo
  8. customResidue was crystallized from ethanol
  9. filtrationSolids were filtered off
  10. washwashed with cold ethanol
  11. customthen dried in vacuo

Sources & evidence

ORD record
ord-87cbbbc8a1ba4ab6aac7c9739a041a51
Source dataset
uspto-grants-2010_11
Patent number
US07834007B2

Reaction notes

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