Triethylamine → HCID 21898176、化合物

HRID 719379ノート

反応式

HRID 719379 の反応式
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.CCN(CC)CC.[Cl:22][S:23](O)(=[O:25])=[O:24].P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH2:11][N:12]([S:23]([Cl:22])(=[O:25])=[O:24])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochloride

生成物 1

HCID 21898176HCID 21898176、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

4-(4Fluoro-phenyl)-piperidine hydrochloride (1.0 g; 4.64 mmol) and Et3N (1.9 ml; 13.9 mmol) was dissolved in DCM (20 ml) and cooled to 0° C. using an ice/water bath. ClSO3H (309 ul; 4.6 mmol) was slowly added droppwise due to highly exothermic reaction. After addition was compleat the mixture was allowed to reach room temperature and stirred over night. The clear yellow solution of the intermediate sulfonicacid derivative was evaporated and dry Toluene (20 ml) was added to form a slurry. To this slurry was added PCl5 (1.06 g; 5.1 mmol) in portions, the mixture was heated on an oil bath to 75° C. for 2 h, and then left over night in room temperature before filtration. The filtercake was washed with Toluene and the filtrate was evaporated. EtOAc was added and precipitating salts was removed by filtration. The crude product was purified on 70 g Si-60 gel using flash chromatography with a gradient 100% Heptane to 100% DCM. Gradient time was 35 min and flow of solvent was 20 ml/min. Fractions containing product was evaporated to give the title compound as a slightly yellow oil that crystallises upon standing. Obtained 0.94 (70% yield) of the title compound.

後処理

  1. additionAfter addition
  2. customto reach room temperature
  3. customThe clear yellow solution of the intermediate sulfonicacid derivative was evaporated
  4. additiondry Toluene (20 ml) was added
  5. customto form a slurry
  6. temperaturethe mixture was heated on an oil bath to 75° C. for 2 h
  7. waitleft over night in room temperature before filtration
  8. washThe filtercake was washed with Toluene
  9. customthe filtrate was evaporated
  10. additionEtOAc was added
  11. customprecipitating salts
  12. customwas removed by filtration
  13. customThe crude product was purified on 70 g Si-60 gel
  14. additionFractions containing product
  15. customwas evaporated

出典と根拠

ORDレコード
ord-ab6e31c8fae546e0b1b7d4d3d619e36d
出典データセット
uspto-grants-2006_11
特許番号
US07132434B2

反応ノート

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