Potassium Carbonate → 1-(3-Methoxy-4-nitrophenyl)piperidin-4-ol

HRID 1014195ノート

反応式

HRID 1014195 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[OH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:17]2[CH2:18][CH2:19][CH:14]([OH:13])[CH2:15][CH2:16]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 27792505-Fluoro-2-nitroanisole

生成物 1

HCID 259188601-(3-Methoxy-4-nitrophenyl)piperidin-4-ol収率 99%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

A mixture of 4-fluoro-2-(methyloxy)-1-nitrobenzene (7.52 g, 44 mmol), 4-hydroxypiperidine (4.45 g, 44 mmol) and potassium carbonate in 100 mL DMSO was stirred for 72 h. The reaction was diluted with water and extracted twice with Ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, and concentrated to give 1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinol (10.9 g, 99% yield). 1H NMR (400 MHz, d6-DMSO) δ 7.84 (d, J=9.2 Hz, 1H), 6.54 (d, J=9.6 Hz, 1H), 6.46 (s, 1H), 4.73 (d, J=4.4 Hz, 1H), 3.86 (s, 3H), 3.80-3.69 (m, 3H), 3.18-3.12 (m, 2H), 1.79-1.76 (m, 2H), 1.42-1.34 (m, 2H).

後処理

  1. extractionextracted twice with Ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-4f3bed9c34dd45d3b46348f3fd703097
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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