Red-Al → (3-Benzylphenyl)methanamine

HRID 23124ノート

反応式

HRID 23124 の反応式
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCO[AlH2-]OCCOC.[Na+].[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[CH2:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[CH2:11][NH2:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 16684438Red-AlHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 222388273-(Benzyl)benzamide

生成物 1

HCID 22312794(3-Benzylphenyl)methanamine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
60 °C

実験手順

To a solution of 3-(benzyl)benzamide (0.0094 moles) from Step B in 70 of toluene was added 8 mL of Red-Al® (65+wt. % solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene, Aldrich) (CAUTION—reaction very exothermic). The reaction mixture was then heated at 60° C. for 2 hours and then poured over ice. The resulting mixture was extracted with ethyl acetate and the combined extracts were washed with water and brine. The organic layer was extracted with 1N HCl and the aqueous layer washed with ethyl acetate. The pH of the aqueous layer was then adjusted to about 9.0 with 1N NaOH and extracted with ethyl acetate. The organic extracts were washed with water and brine and then concentrated to give 3-(benzyl)benzyl amine.

後処理

  1. additionpoured over ice
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe combined extracts were washed with water and brine
  4. extractionThe organic layer was extracted with 1N HCl
  5. washthe aqueous layer washed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe organic extracts were washed with water and brine
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-a4ef589c69c0442a98e17b791daeca52
出典データセット
uspto-grants-2005_02
特許番号
US06849650B2

反応ノート

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