Sodium Hydroxide → 1-Benzyl-4-methyl-4-phenylpiperidine

HRID 322157ノート

反応式

HRID 322157 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[OH-].[Na+]>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 108459131-Benzyl-4-methylpiperidin-4-ol

生成物 1

HCID 108016621-Benzyl-4-methyl-4-phenylpiperidine収率 104%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

1-Benzyl-4-methylpiperidin-4-ol (4.81 g, 23.4 mmol, 1.00 equiv) was added to a suspension of AlCl3 (15.62 g, 117 mmol, 5.00 equiv) in benzene (100 mL) at room temperature under argon. The mixture was stirred at reflux for 24 hours, then cooled and poured cautiously into ice water (100 g of ice plus 50 mL of water). The aqueous phase was adjusted to pH 11-12 by addition of 6N aqueous NaOH at 0° C., and extracted with EtOAc (3×100 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, hexane-Et2O 19:1 to 9:1 followed by hexane-EtOAc 3:1) to give 3.23 g (52%) of brown oil, which was characterized spectroscopically.

後処理

  1. temperatureat reflux for 24 hours
  2. temperaturecooled
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic solutions were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (SiO2, hexane-Et2O 19:1 to 9:1 followed by hexane-EtOAc 3:1)

出典と根拠

ORDレコード
ord-e63088929bf3495e8c42a7d4de85e22a
出典データセット
uspto-grants-2001_04
特許番号
US06211198B1

反応ノート

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