2-Amino-1-(3-chlorophenyl)ethan-1-ol → N-[3-(4-Methylphenyl)-1-methylpropyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine

HRID 280303노트

반응식

HRID 280303 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=O)[CH3:11])=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:20]([OH:23])[CH2:21][NH2:22])[CH:17]=[CH:18][CH:19]=1>C1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([NH:22][CH2:21][CH:20]([OH:23])[C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([Cl:13])[CH:15]=2)[CH3:11])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 54639084-(p-Tolyl)-2-butanone

생성물 1

HCID 23322179N-[3-(4-Methylphenyl)-1-methylpropyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A mixture of 4-(4-Methylphenyl)butan-2-one (1.62 g) and 2-(3-chlorophenyl)-2-hydroxyethanamine (1.71 g) was refluxed in benzene under Dean & Stark conditions for 4 h. The solvent was removed under reduced pressure, replaced with methanol (100 ml) and sodium borohydride (2 g) added portionwise. The solvent was evaporated under reduced pressure, the residue partitioned between water and ether and the ether layer dried (MgSO4). Removal of the solvent gave an oil which was chromatographed on Kieselgel 60. Elution with 1% methanol-chloroform gave the title compound as an 11:89 mixture of diastereoisomers, mp 75-106 (hexane).

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionadded portionwise
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue partitioned between water and ether
  5. dry with materialthe ether layer dried (MgSO4)
  6. customRemoval of the solvent
  7. customgave an oil which
  8. customwas chromatographed on Kieselgel 60
  9. washElution with 1% methanol-chloroform

출처 및 근거

ORD 기록
ord-d6084b572ab14f168a71bb533a351aeb
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588749

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