Isoamylamine → (4-Bromo-2-chloro-benzyl)-(3-methyl-butyl)-amine

HRID 1435063

반응식

HRID 1435063 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([Cl:10])[CH:3]=1.[CH2:11]([NH2:16])[CH2:12][CH:13]([CH3:15])[CH3:14].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:16][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[C:4]([Cl:10])[CH:3]=1

참가 물질

5

반응물 3

HCID 7894IsoamylamineHCID 4311764Sodium borohydrideHCID 141091094-Bromo-2-chlorobenzaldehyde

생성물 1

HCID 57937814(4-Bromo-2-chloro-benzyl)-(3-methyl-butyl)-amine수율 95%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

4-bromo-2-chloro-benzaldehyde (I-3a: 10.0 g, 46.0 mmol) was dissolved in methanol and treated with isoamylamine (4.78 g, 54.7 mmol). After stirring overnight at room temperature, sodium borohydride (5.2 g, 138 mmol) was added to the reaction mixture. After stirring for 1 hour at room temperature, the reaction mixture was quenched using concentrated (37%) hydrochloric acid and the volatiles were removed under reduced pressure. The residue was taken up in an aqueous 2 N sodium hydroxide solution and extracted with ethyl acetate (2 times). The combined organic phases were washed with a saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title product (I-3b: 12.7 g)

후처리

  1. stirringAfter stirring for 1 hour at room temperature
  2. customthe reaction mixture was quenched
  3. concentrationusing concentrated (37%) hydrochloric acid
  4. customthe volatiles were removed under reduced pressure
  5. extractionextracted with ethyl acetate (2 times)
  6. washThe combined organic phases were washed with a saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3091268a30c3421598847dc60ee415d1
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615651B2

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