Water → Tert-butyl 4-(4-formyl-2-methoxyphenyl)piperazine-1-carboxylate

HRID 336832

反応式

HRID 336832 の反応式
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)=[C:3]([O:10][CH3:11])[CH:4]=1)=[O:7]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27373584-Fluoro-3-methoxybenzaldehyde

生成物 1

HCID 86671380Tert-butyl 4-(4-formyl-2-methoxyphenyl)piperazine-1-carboxylate収率 51%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
90 °C

実験手順

To 400 mg (2.60 mmol) of 4-fluoro-3-methoxybenzaldehyde diluted in 10 ml of dimethylsulfoxide are respectively added 483 mg (2.60 mmol) of tert-butyl piperazine-1-carboxylate, then 394 mg (2.85 mmol) of potassium carbonate. The solution is heated to 90° C. for 40 h, then water is added and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The residue obtained is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 8:2) to yield 425 mg of tert-butyl 4-(4-formyl-2-methoxyphenyl)piperazine-1-carboxylate in the form of a colourless oil.

後処理

  1. extractionthe product is extracted several times with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue obtained
  5. customis purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 8:2)

出典と根拠

ORDレコード
ord-d758faf30d914d1d943e1c7686ed1efc
出典データセット
uspto-grants-2014_11
特許番号
US08889711B2

関連ノート

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