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Formaldehyde → (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[N'-methyl-3-(3-thienyl)benzylamino]benzylamine

HRID 2254413
ノート
印刷プレビュー

反応式

HRID 2254413 の反応式
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[CH:30]=[CH:29][S:28][CH:27]=3)[CH:21]=2)[CH:13]=1)[CH2:9][CH3:10].C=O.[C:35]([BH3-])#N.[Na+]>C(#N)C>[CH3:32][C:2]([CH3:31])([CH3:1])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N:18]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[CH:30]=[CH:29][S:28][CH:27]=3)[CH:21]=2)[CH3:35])[CH:13]=1)[CH2:9][CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 19744695HCID 19744695、化合物

生成物 1

HCID 86747105(E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[N'-methyl-3-(3-thienyl)benzylamino]benzylamine収率 53.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

100 mg of the (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[3-(3-thienyl)benzylamino]benzylamine obtained in Example 175 was dissolved in 3 ml of acetonitrile. 0.1 ml of a 35% aqueous solution of formaldehyde and 22.7 mg of sodium cyanoborohydride were added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was evaporated under reduced pressure. The residue was dissolved in a mixture of ethyl acetate and water. The organic layer was separated, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated. The residue was purified by silica gel column chromatography [Wakogel C-200, 5 g; eluting solvent: hexane/ethyl acetate=10/1→6/1] to give 55 mg (yield 53%) of the captioned compound as a pale yellow crystalline solid, m.p. 51°-52° C.

後処理

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccant was separated by filtration
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography [Wakogel C-200, 5 g; eluting solvent: hexane/ethyl acetate=10/1→6/1]

出典と根拠

ORDレコード
ord-912815c575d1446a9c6a41f887f89e56
出典データセット
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05234946

反応ノート

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