Water → N-Ethyl-4-chlorobenzylamine

HRID 408585노트

반응식

HRID 408585 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH2:10]([NH2:12])[CH3:11].O.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:12][CH2:10][CH3:11])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6341EthylamineHCID 77264-ChlorobenzaldehydeHCID 4311764Sodium borohydride

생성물 1

HCID 580651N-Ethyl-4-chlorobenzylamine

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
20 °C

실험 절차

To a solution of 4-chlorobenzaldehyde (1 eq.) in MeOH was added ethylamine 70% in water (10 eq.). The reaction was stirred for 15 h at 20° C. under argon then NaBH4 (2 eq.) was added. The reaction was stirred at 20° C. for 5 h. The reaction was quenched with water then acidified with aqueous HCl (2M). The aqueous layer was washed with EtOAc. The organic layer was discarded. Aqueous NaOH (2M) was then added to the aqueous layer until pH=10 and the crude was extracted twice with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford (4-chloro-benzyl)-ethyl-amine.

후처리

  1. stirringThe reaction was stirred at 20° C. for 5 h
  2. customThe reaction was quenched with water
  3. washThe aqueous layer was washed with EtOAc
  4. additionAqueous NaOH (2M) was then added to the aqueous layer until pH=10
  5. extractionthe crude was extracted twice with EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9cbdd250aa5e45388d9c0e02b231ef54
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759334B2

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