Ethanolamine → 2-(4-Chloro-benzylamino)-ethanol

HRID 408588

반응식

HRID 408588 반응식
[CH2:1]([CH2:3][NH2:4])[OH:2].C([O-])(O)=O.[Na+].[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[BH4-].[Na+]>C1COCC1.CO>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:4][CH2:3][CH2:1][OH:2])=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 700EthanolamineHCID 77264-ChlorobenzaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

생성물 1

HCID 4244522-(4-Chloro-benzylamino)-ethanol

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of ethanolamine (1.2 eq.) in either MeOH or THF were added NaHCO3 (1.5 eq.) and 4-chlorobenzaldehyde (1 eq.). The reaction was refluxed for 4 h, then cooled to 0° C. NaBH4 (1.2 eq.) was added portionwise. The reaction was stirred for 1 h at 0° C., then 15 h at 20° C. The crude was concentrated under reduced pressure then partitioned between water and DCM. The aqueous layer was then extracted twice with DCM. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with DCM/MeOH: 1/0 to 95/5) to afford 2-(4-chloro-benzylamino)-ethanol.

후처리

  1. temperatureThe reaction was refluxed for 4 h
  2. custom15 h
  3. customat 20° C
  4. concentrationThe crude was concentrated under reduced pressure
  5. customthen partitioned between water and DCM
  6. extractionThe aqueous layer was then extracted twice with DCM
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude was purified by chromatography on silica gel (elution with DCM/MeOH: 1/0 to 95/5)

출처 및 근거

ORD 기록
ord-bc4addb90c7f49ce91f792e1b8b06d90
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759334B2

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