Potassium Carbonate → HCID 68494469、化合物

HRID 453885ノート

反応式

HRID 453885 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-c3d5420be44f4e40b0d0aa12c202f63b
出典データセット
uspto-grants-2013_07
特許番号
US08492559B2

反応ノート

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