Water → (3S)-2-methyl-4-{4-[3-(3-methylpiperidin-1-yl)propoxy]phenyl}pyridine 1-oxide

HRID 657659ノート

反応式

HRID 657659 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N+:11]([O-:14])=[C:10]([CH3:15])[CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.CS(O[CH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][CH2:34][C@H:33]([CH3:37])[CH2:32]1)(=O)=O.O>CN(C)C=O>[CH3:15][C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][C@H:33]([CH3:37])[CH2:32]3)=[CH:7][CH:6]=2)[CH:13]=[CH:12][N+:11]=1[O-:14]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 86629975(3S)-1-(3-methane-sulfonyloxypropyl)-3-methylpiperidine hydrochlorideHCID 178422725HCID 178422725、化合物

生成物 1

HCID 15940923(3S)-2-methyl-4-{4-[3-(3-methylpiperidin-1-yl)propoxy]phenyl}pyridine 1-oxide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A A mixture of 4-(4-hydroxyphenyl)-2-methylpyridine 1-oxide (55 mg), potassium carbonate (187 mg) and (3S)-1-(3-methanesulfonyloxypropyl)-3-methylpiperidine hydrochloride in N,N-dimethylformamide (3 mL) is heated at a temperature close to 65° C. overnight and cooled back to room temperature. Water (5 mL) is added; the solution is washed with methylcyclohexane (twice 10 mL) and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (eluent dichloromethane/methanol from 95/5 to 80/20). Fraction containing the expected product are pooled and concentrated under reduced pressure. The crude base is diluted in ethanol, oxalic acid (7 mg) is added and solvent is removed under reduced pressure to give 32 mg of (3S)-2-methyl-4-{4-[3-(3-methylpiperidin-1-yl)propoxy]phenyl}pyridine 1-oxide, oxalate as a brown crystalline material.

後処理

  1. temperatureis heated at a temperature
  2. customclose to 65° C. overnight
  3. washthe solution is washed with methylcyclohexane (twice 10 mL)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography over silica gel (eluent dichloromethane/methanol from 95/5 to 80/20)
  6. additionFraction containing the expected product
  7. concentrationconcentrated under reduced pressure
  8. additionThe crude base is diluted in ethanol
  9. additionoxalic acid (7 mg) is added
  10. customsolvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-4c40da2760804c0f8eb8014fbb2767e9
出典データセット
uspto-grants-2011_12
特許番号
US08076329B2

反応ノート

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