Sodium Hydroxide → (4-Nitrobenzyl)dipropylamine

HRID 348598

反応式

HRID 348598 の反応式
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].[OH-].[Na+]>C(Cl)(Cl)Cl>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:7][CH2:8][CH3:9])[CH2:6][CH2:5][CH3:12])=[CH:11][CH:12]=1)([O-:4])=[O:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 112524674-Nitrobenzylamine hydrochloride

生成物 1

HCID 15871689(4-Nitrobenzyl)dipropylamine収率 146.5%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Commercially available 4-nitrobenzylamine hydrochloride (manufactured by Tokyo Kasei Kogyo., Ltd.) (1.82 g) was suspended in chloroform (15 ml). Then, a 1 mol/l sodium hydroxide aqueous solution (15 ml) was added to the suspension and the aqueous layer was then extracted with chloroform. The extract was dried with anhydrous magnesium sulfate and the solvent was then distilled off, followed by dissolving the residue in anhydrous methanol (20 ml). Subsequently, the solution was added with propionaldehyde (1.66 ml) and sodium cyanoborohydride (1.81 g) and then adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 21 hours. After completion of the reaction, the solvent was distilled off. The residue was added with 1 mol/l sodium hydroxide and then subjected to chloroform extraction. The extract was dried with anhydrous magnesium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (1.67 g) as a yellow oily substance.

後処理

  1. extractionthe aqueous layer was then extracted with chloroform
  2. dry with materialThe extract was dried with anhydrous magnesium sulfate
  3. distillationthe solvent was then distilled off
  4. dissolutionby dissolving the residue in anhydrous methanol (20 ml)
  5. additionSubsequently, the solution was added with propionaldehyde (1.66 ml) and sodium cyanoborohydride (1.81 g)
  6. customAfter completion of the reaction
  7. distillationthe solvent was distilled off
  8. additionThe residue was added with 1 mol/l sodium hydroxide
  9. extractionsubjected to chloroform extraction
  10. dry with materialThe extract was dried with anhydrous magnesium sulfate
  11. distillationthe solvent was then distilled off
  12. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-f296b0df65594fbfab96bd3485f2094c
出典データセット
uspto-grants-2007_02
特許番号
US07176227B2

関連ノート

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