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

HRID 1172362노트

반응식

HRID 1172362 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-87cbbbc8a1ba4ab6aac7c9739a041a51
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834007B2

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