4-(2-Bromoethyl)phenol → 3-(r,s)-(1-Carbamoyl-1,1-diphenylmethyl)-1-(4-hydroxyphenethyl)piperidine

HRID 21399

반응식

HRID 21399 반응식
[C:1]([C:4]([CH:17]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[NH2:2].[OH:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29]Br)=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]([C:4]([CH:17]1[CH2:22][CH2:21][CH2:20][N:19]([CH2:29][CH2:28][C:27]2[CH:31]=[CH:32][C:24]([OH:23])=[CH:25][CH:26]=2)[CH2:18]1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[NH2:2]

참가 물질

5

반응물 3

HCID 842214-(2-Bromoethyl)phenolHCID 516892Sodium BicarbonateHCID 136337483-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)piperidine

생성물 1

HCID 212240793-(r,s)-(1-Carbamoyl-1,1-diphenylmethyl)-1-(4-hydroxyphenethyl)piperidine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)piperidine (0.3 g), 4-hydroxyphenethyl bromide (0.21 g), sodium bicarbonate (0.3 g) and acetonitrile (15 ml) was heated under reflux for 5 hours. The mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml), the layers separated, and the aqueous layer extracted with dichloromethane (2×50 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a gum which was purified by column chromatography, firstly on silica eluting with dichlorometbane containing methanol (0% up to 6%), and then on alumina eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as colourless microcrystals, yield 0.042 g, m.p. 135°-140° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×50 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a gum which
  9. customwas purified by column chromatography, firstly on silica eluting with dichlorometbane
  10. additioncontaining methanol (0% up to 6%)
  11. additionon alumina eluting with dichloromethane containing methanol (0% up to 10%)
  12. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2495e3683f3f4471978788ad6a5706b0
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05422358

연결된 노트

불러오는 중…