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

HRID 2099101ノート

反応式

HRID 2099101 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 64854035-Fluoro-2-piperidin-1-yl-phenylamine収率 100.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6806df6ba3bb4118a5f2244c57a95fe2
出典データセット
uspto-grants-2009_08
特許番号
US07569536B2

反応ノート

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