Water → 1-Aminocarbonyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

HRID 248869

反応式

HRID 248869 の反応式
[F:1][C:2]1[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[N+]([NH:22][C:23](N)=[O:24])([O-])=O.O>C(O)C>[NH2:22][C:23]([N:8]1[CH2:9][CH2:10][CH:5]([O:4][C:3]2[C:11]([F:18])=[C:12]([F:17])[C:13]([F:16])=[C:14]([F:15])[C:2]=2[F:1])[CH2:6][CH2:7]1)=[O:24]

参加物

5

反応物 3

HCID 962WaterHCID 62372NitroureaHCID 148370404-(2,3,4,5,6-Pentafluorophenoxy)piperidine

生成物 1

HCID 197624621-Aminocarbonyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine収率 73.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
65 °C

実験手順

A solution of 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine in 100 ml of 95% ethanol was treated with 1.73 g of nitrourea and then stirred at 65° C. for five hours. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Filtration, followed by evaporation of the solvents afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with 5% methanol/dichloromethane). The resultant solid was recrystallized from hot isopropanol to yield 3.41 g (73.3%) of 1-aminocarbonyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine, m.p. 170°-172° C.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation of the solvents
  7. customafforded a residue which
  8. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 5% methanol/dichloromethane)
  9. customThe resultant solid was recrystallized from hot isopropanol

出典と根拠

ORDレコード
ord-9d6390a6c1ee4c4f86c013f205aa450a
出典データセット
uspto-grants-1993_05
特許番号
US05212184

関連ノート

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