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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
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HRID 2254413 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 19744695HCID 19744695, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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]

출처 및 근거

ORD 기록
ord-912815c575d1446a9c6a41f887f89e56
출처 데이터셋
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05234946

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