Potassium Carbonate → HCID 68494469、化合物

HRID 1500328ノート

反応式

HRID 1500328 の反応式
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9]Br)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:18][N:19]([CH3:31])[C:20]1([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.CO.C(Cl)(Cl)Cl>C1COCC1>[CH3:18][N:19]([CH3:31])[C:20]1([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][N:23]([CH2:9][CH2:8][NH:7][C:6](=[O:11])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:22][CH2:21]1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 21584188Chloroform methanolHCID 57831263HCID 57831263、化合物

生成物 1

HCID 68494469HCID 68494469、化合物収率 76.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

11.1 g (1.5 eq) tert-butyl-2-bromoethylcarbamate dissolved in 65 ml THF and 9.19 g (2 eq) potassium carbonate were added to a solution of 7 g (1 eq) N,N-dimethyl-4-(thiophen-2-yl)piperidin-4-amine in 40 ml THF. The reaction mixture was heated for 6 h at 70° C. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). Once the conversion was complete, the solvent was distilled off completely, the residue mixed with 200 ml water and the aqueous phase extracted with 20% IPA/CHCl3. The combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel; 10% MeOH/CHCl3). 9 g (76%) of product were obtained in the form of an oil.

後処理

  1. distillationthe solvent was distilled off completely
  2. additionthe residue mixed with 200 ml water
  3. extractionthe aqueous phase extracted with 20% IPA/CHCl3
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customremoval of the solvent under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel; 10% MeOH/CHCl3)

出典と根拠

ORDレコード
ord-cee7b282dd2244a0a7f0d2404e018484
出典データセット
uspto-grants-2015_12
特許番号
US09206156B2

反応ノート

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