Methanol → 2-(4-Methoxyphenethylamino)cyclohexanol

HRID 228334

반응식

HRID 228334 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[OH:8].C([O-])([O-])=O.[K+].[K+].Cl[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.CO>CN(C=O)C>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[OH:8])=[CH:19][CH:20]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 232862-AminocyclohexanolHCID 875134-(2-Chloroethyl)phenyl methyl ether

생성물 1

HCID 607146502-(4-Methoxyphenethylamino)cyclohexanol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

Mix (±)-2-aminocyclohexanol (1.5227 g, 13.2 mmol), K2CO3 (4.56 g, 33.0 mmol), and 1-(2-chloroethyl)-4-methoxybenzene (2.0 mL, 13.2 mmol) in DMF (30 mL). Heat at 100° C. for 24 hours. Cool down to room temperature and filtrate with MeOH wash. Concentrate and remove DMF azeotropically with xylenes. Take up the residue in CH2C2 and H2O (100 mL each). Separate the layers and extract the aqueous layer with CH2Cl2 (2×100 mL). Wash the organic layers with H2O and brine (100 mL each). Dry the combined organic layers over MgSO4, concentrate and purify by flash chromatography, eluting with 50:45:5 EtOAc/CH2Cl/2.0 M NH3 in MeOH to afford 2-(4-methoxyphenethylamino)cyclohexanol. (1.38 g, 42%).

후처리

  1. washwash
  2. concentrationConcentrate
  3. customremove DMF azeotropically with xylenes
  4. customSeparate the layers
  5. extractionextract the aqueous layer with CH2Cl2 (2×100 mL)
  6. washWash the organic layers with H2O and brine (100 mL each)
  7. dry with materialDry the combined organic layers over MgSO4
  8. concentrationconcentrate
  9. custompurify by flash chromatography
  10. washeluting with 50:45:5 EtOAc/CH2Cl/2.0 M NH3 in MeOH

출처 및 근거

ORD 기록
ord-7b727e9032f0430099b8f30e0642387b
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560463B2

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