Water → 3-(Piperidin-1-yl)phenol

HRID 1516144ノート

反応式

HRID 1516144 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:1]1([C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

参加物

7

反応物 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 115683-AminophenolHCID 516892Sodium Bicarbonate

生成物 1

HCID 2298553-(Piperidin-1-yl)phenol収率 73%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

10.91 g (100 mmol) of 3-aminophenol was dissolved in 100 ml of toluene, and 18.5 g (220 mmol) of sodium bicarbonate and 16.0 ml (110 mmol) of 1,5-dibromopentane were added thereto, followed by refluxing the resulting mixture for 17 hours. The reaction mixture was cooled to room temperature, and 100 ml of water and 100 ml of ethyl acetate were added thereto. The water layer was separated, extracted twice with 100 ml portions of ethyl acetate, and the organic layers were combined, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The concentrate was subjected to column chromatography using 20% ethyl acetate/hexane as an eluent to obtain 12.9 g (yield 73%) of 3-(piperidin-1-yl)phenol as a solid.

後処理

  1. temperatureby refluxing the resulting mixture for 17 hours
  2. customThe water layer was separated
  3. extractionextracted twice with 100 ml portions of ethyl acetate
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under a reduced pressure

出典と根拠

ORDレコード
ord-c3b3bf78f1c746b1b065eaf16d72e4b1
出典データセット
uspto-grants-2012_07
特許番号
US08227456B2

反応ノート

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