Sodium Hydroxide → alpha,alpha-Dimethyl-2-naphthaleneethanamine

HRID 1349443노트

반응식

HRID 1349443 반응식
[CH3:1][C:2]([NH:15]C(OCC1C=CC=CC=1)=O)([CH3:14])[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.[OH-].[Na+]>CO.O.[OH-].[OH-].[Pd+2]>[CH3:14][C:2]([NH2:15])([CH3:1])[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 9923712n-[2-Methyl-1-(naphthalen-2-yl)propan-2-yl]-benzyloxycarboxamide

생성물 1

HCID 15369616alpha,alpha-Dimethyl-2-naphthaleneethanamine수율 97.2%

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매2회HCID 962Water용매

실험 절차

Palladium hydroxide on carbon (19.7 g) was suspended in methanol (500 ml), to the suspension was added a solution of N-[2-methyl-1-(naphthalen-2-yl)propan-2-yl]-benzyloxycarboxamide (237.6 g) obtained in Step 11 in methanol (2 L), and a hydrogenation reaction was performed at room temperature overnight. After filtration of the reaction mixture, the filtrate was concentrated under reduced pressure. To the obtained residue was added ethyl acetate, and to the solution was added conc. hydrochloric acid (70 ml) to give crystals. The obtained crystals were suspended in water, and after an addition of 4N aqueous sodium hydroxide solution (350 ml), the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crystals of the title compound (138 g).

후처리

  1. customa hydrogenation reaction
  2. filtrationAfter filtration of the reaction mixture
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the obtained residue was added ethyl acetate
  5. additionto the solution was added conc. hydrochloric acid (70 ml)
  6. customto give crystals
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3782ee51b10e4d96b11130655e32eaf5
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211685B2

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