Methanol → 2-Acetylamino-5-(3-piperidin-1-ylpropoxy)benzoic acid methyl ester

HRID 1157447노트

반응식

HRID 1157447 반응식
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13]OS(C)(=O)=O)[CH:7]=[CH:6][C:5]=1[NH:19][C:20](=[O:22])[CH3:21].[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C([O-])([O-])=O.[K+].[K+].CO>C(#N)C>[NH4+:19].[OH-:2].[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:7]=[CH:6][C:5]=1[NH:19][C:20](=[O:22])[CH3:21]

참가 물질

7

반응물 4

HCID 887MethanolHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 866229032-Acetylamino-5-(3-methanesulfonyloxypropoxy)benzoic acid methyl ester

생성물 2

HCID 14923Ammonium HydroxideHCID 685239932-Acetylamino-5-(3-piperidin-1-ylpropoxy)benzoic acid methyl ester수율 61%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of the crude 2-acetylamino-5-(3-methanesulfonyloxypropoxy)benzoic acid methyl ester, piperidine (1.28 mL, 12.9 mmol) and K2CO3 (1.07 g, 7.7 mmol) in acetonitrile (12 mL) was heated at reflux temperature for 16 h. This reaction mixture was concentrated in vacuo and the crude residue partitioned between dichloromethane and water. The aqueous was extracted with dichloromethane (3×50 mL) and the combined organics washed with brine (1×50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel with dichloromethane:methanol:NH4OH (aq.) (180:19:1, v/v) as eluent to provide 2-acetylamino-5-(3-piperidin-1-ylpropoxy)benzoic acid methyl ester (526 mg, 1.6 mmol, 61% from 2-acetylamino-5-(3-hydroxypropoxy)benzoic acid methyl ester).

후처리

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 h
  3. concentrationThis reaction mixture was concentrated in vacuo
  4. customthe crude residue partitioned between dichloromethane and water
  5. extractionThe aqueous was extracted with dichloromethane (3×50 mL)
  6. washthe combined organics washed with brine (1×50 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel with dichloromethane

출처 및 근거

ORD 기록
ord-22168d4ded754f0f822220c5ba9d267c
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807686B2

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