Hydrochloric Acid → 5-Fluoro-2-piperidin-1-yl-phenylamine

HRID 2099101노트

반응식

HRID 2099101 반응식
Cl.[Sn](Cl)Cl.[F:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:8]([N+:18]([O-])=O)[CH:7]=1.C(=O)(O)[O-].[Na+]>CO>[F:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:8]([CH:7]=1)[NH2:18]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 27374341-(4-fluoro-2-nitrophenyl)piperidine

생성물 1

HCID 64854035-Fluoro-2-piperidin-1-yl-phenylamine수율 100.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Concentrated hydrochloric acid (1.20 ml, 14.4 mmol) and anhydrous tin dichloride (1.22 g, 6.43 mmol) were sequentially added at 0° C. to a methanol (5 ml) solution of 1-(4-fluoro-2-nitrophenyl)piperidine (289 mg, 1.28 mmol), obtained as described in Referential Example 17-1. The resulting mixture was warmed to room temperature and stirred for 21 hours. A saturated aqueous solution of sodium bicarbonate was added to the mixture. The mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (25 g, hexane/ethyl acetate=12/1). Thus, 5-fluoro-2-(1-piperidinyl)aniline (250 mg, quant.) was yielded as a colorless oily material.

후처리

  1. customobtained
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. washThe obtained organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (25 g, hexane/ethyl acetate=12/1)

출처 및 근거

ORD 기록
ord-6806df6ba3bb4118a5f2244c57a95fe2
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569536B2

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