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

HRID 2195654

反応式

HRID 2195654 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

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

出典と根拠

ORDレコード
ord-64bfcd7d36214e43a1c21ed88b8a3bbd
出典データセット
uspto-grants-2012_12
特許番号
US08338362B2

関連ノート

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