2-Amino-1-(3-chlorophenyl)ethan-1-ol → 3-Chloro-alpha-[[[2-[4-(3-pyridylmethyloxy)phenyl]-1-methylethyl]amino]methyl]benzenemethanol

HRID 465424노트

반응식

HRID 465424 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](=O)[CH3:17])=[CH:11][CH:10]=2)[CH:2]=1.[OH:19][CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1)[CH2:21][NH2:22]>O>[Cl:29][C:25]1[CH:24]=[C:23]([CH:20]([CH2:21][NH:22][CH:16]([CH3:17])[CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:10][CH:11]=2)[OH:19])[CH:28]=[CH:27][CH:26]=1

참가 물질

4

반응물 2

HCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 19874530[4-(3-Pyridylmethyloxy)phenyl]propan-2-one

생성물 1

HCID 198745693-Chloro-alpha-[[[2-[4-(3-pyridylmethyloxy)phenyl]-1-methylethyl]amino]methyl]benzenemethanol수율 54.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 1-[4-(3-pyridylmethyloxy)phenyl]propan-2-one (7.2 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (5.1 g) was boiled under reflux with azeotropic removal of water until the reaction was complete. The solvent was evaporated, the residue dissolved in methanol (150 ml), cooled in an ice-bath and treated with sodium borohydride (5 g). After stirring for 1 hour the methanol was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with water, dried and evaporated to give an oil which was chromatographed on Kieselgel 60. Elution with 3% methanol in chloroform gave a yellow oil (6.4 g). Bulb to bulb distillation of this oil gave 3-chloro-β-[[[2-[4-(3-pyridylmethyloxy)phenyl]-1-methylethyl]amino]methyl]benzenemethanol b.p. 120°-130° C./0.4 mm, as a 1:1 mixture of diastereoisomers.

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol (150 ml)
  3. temperaturecooled in an ice-bath
  4. additiontreated with sodium borohydride (5 g)
  5. customwas evaporated
  6. customthe residue partitioned between ethyl acetate and water
  7. washThe organic phase was washed with water
  8. customdried
  9. customevaporated
  10. customto give an oil which
  11. customwas chromatographed on Kieselgel 60
  12. washElution with 3% methanol in chloroform

출처 및 근거

ORD 기록
ord-2a926d5b8195484bbad19fff3e7c2b87
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153210

반응 노트

불러오는 중…