Hydrochloric Acid → 5-Chloro-2-(piperidin-1-yl)aniline

HRID 2099095

Reaktionsgleichung

Reaktionsgleichung von HRID 2099095
Cl.[Sn](Cl)Cl.[Cl: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>[Cl: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]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 2853181-(4-Chloro-2-nitrophenyl)piperidineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 2853175-Chloro-2-(piperidin-1-yl)anilineAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Concentrated hydrochloric acid (2.00 ml, 24.0 mmol) and anhydrous tin dichloride (1.84 g, 9.70 mmol) were sequentially added at 0° C. to a methanol (10 ml) solution of 1-(4-chloro-2-nitrophenyl)piperidine (471 mg, 1.95 mmol), obtained as described in Referential Example 15-1. The resulting mixture was warmed to room temperature and stirred for 16 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 (30 g, hexane/ethyl acetate=9/1). Thus, 5-chloro-2-(1-piperidinyl)aniline (388 mg, 94.3%) was yielded as a colorless oily material.

Aufarbeitung

  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 (30 g, hexane/ethyl acetate=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-dffb36988b4c4892ba46b6ab2b71e88d
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569536B2

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