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Diisobutylaluminum hydride → N1-Methyl-1-phenylethylenediamine

HRID 1092364
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HRID 1092364 반응식
[CH3:1][NH:2][C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(C)[C:4]#[N:5].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:1][NH:2][CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:4][NH2:5]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 14487Diisobutylaluminum hydrideHCID 137749972-Methylamino-2-phenyl-propionitrile

생성물 1

HCID 98060N1-Methyl-1-phenylethylenediamine수율 106.7%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

A solution of 2-methylamino-2-phenyl-propionitrile (7.8 g) in toluene (60 mL) was cooled to −78° C. and DIBAL-H solution (104 mL of a 20% solution in toluene) was added drop wise under nitrogen. The reaction mixture was slowly warmed to room temperature and then left at stirring for 17 h. After completion, the reaction mixture was quenched with 30 mL methanol and then 100 mL water. All solvents were evaporated and crude material was taken into 50 mL of water and acidified to pH=1 with 1N HCl. The mixture was extracted with ethyl acetate and separated, and the aqueous layer was basified to pH=14 with 30% NaOH solution. The free diamine was extracted with dichloromethane, dried over sodium sulfate, filtered and concentrated to obtain the desired known N1-methyl-1-phenylethane-1,2-diamine (CAS 66308-14-3) (7.8 g) which was used in the next step without further purification.

후처리

  1. waitleft
  2. customAfter completion, the reaction mixture was quenched with 30 mL methanol
  3. customAll solvents were evaporated
  4. extractionThe mixture was extracted with ethyl acetate
  5. customseparated
  6. extractionThe free diamine was extracted with dichloromethane
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7e12004bca0c4711ab5a21f202882ffe
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129423B2

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