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

HRID 1157447ノート

反応式

HRID 1157447 の反応式
[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]

参加物

7

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-22168d4ded754f0f822220c5ba9d267c
出典データセット
uspto-grants-2010_10
特許番号
US07807686B2

反応ノート

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