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

HRID 2195654

반응식

HRID 2195654 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 2853175-Chloro-2-(piperidin-1-yl)aniline수율 94.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

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

출처 및 근거

ORD 기록
ord-64bfcd7d36214e43a1c21ed88b8a3bbd
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338362B2

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