Hydrochloric Acid → 2-(Piperidin-1-yl)aniline

HRID 2195663노트

반응식

HRID 2195663 반응식
Cl.[Sn](Cl)Cl.[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)([O-])=O.C(=O)(O)[O-].[Na+]>CO>[N:14]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH2:5])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 2254571-(2-Nitrophenyl)piperidineHCID 516892Sodium Bicarbonate

생성물 1

HCID 4587952-(Piperidin-1-yl)aniline수율 88.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Concentrated hydrochloric acid (1.50 ml, 18.0 mmol) and anhydrous tin dichloride (1.45 g, 7.64 mmol) were sequentially added at 0° C. to a methanol (10 ml) solution of 1-(2-nitrophenyl)piperidine (315 mg, 1.52 mmol) obtained as described in Referential Example 18-1. The resulting mixture was warmed to room temperature and stirred for 17 hours. A saturated aqueous solution of sodium bicarbonate was added to the mixture. The resulting 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 (20 g, hexane/ethyl acetate=15/1). Thus, 2-(1-piperidinyl)aniline (238 mg, 88.8%) was yielded as a pale yellow oily material.

후처리

  1. customobtained
  2. extractionThe resulting 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 (20 g, hexane/ethyl acetate=15/1)

출처 및 근거

ORD 기록
ord-5a1f652a23a54039aae61f6fdba033ba
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338362B2

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