Phenacyl bromide → Tert-butyl 4-methyl-3-(4-phenylthiazol-2-yl)piperazine-1-carboxylate

HRID 874969ノート

反応式

HRID 874969 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[C:11]([CH:14]1[N:19]([CH3:20])[CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15]1)(=[S:13])[NH2:12]>CCO>[CH3:20][N:19]1[CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[CH2:15][CH:14]1[C:11]1[S:13][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:12]=1

参加物

4

反応物 2

HCID 6259Phenacyl bromideHCID 86673534HCID 86673534、化合物

生成物 1

HCID 70975633Tert-butyl 4-methyl-3-(4-phenylthiazol-2-yl)piperazine-1-carboxylate収率 64.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

A mixture of 2-bromoacetophenone (130 mg, 0.65 mmol) and tert-butyl 3-carbamothioyl-4-methylpiperazine-1-carboxylate (170 mg, 0.65 mmol) in EtOH (15 mL) was heated to 70° C. for 4 h. The reaction mixture was cooled to room temperature and solvent was evaporated under reduced pressure. The residue was diluted with water and the organic product was extracted with EtOAc. The combined extracts were washed with H2O and brine, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 20-25% EtOAc in petroleum ether) to afford tert-butyl 4-methyl-3-(4-phenylthiazol-2-yl)piperazine-1-carboxylate (150 mg, yield 64%). 1H NMR (300 MHz, CDCl3) δ 7.92-7.90 (m, 2H), 7.49 (m, 1H), 7.46-7.41 (m, 2H), 7.37-7.34 (m, 1H), 4.03-3.98 (m, 1H), 3.67-3.64 (m, 2H), 3.23-3.15 (m, 2H), 2.97-2.93 (m, 2H), 2.26 (s, 3H), 1.46 (s, 9H). MS (ESI) m/z: Calculated for C19H25N3O2S: 359.17. found: 360.2 (M+H)+

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customsolvent was evaporated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionthe organic product was extracted with EtOAc
  5. washThe combined extracts were washed with H2O and brine
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 20-25% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-48d68d5e72474c058cf12631ab5ea7cc
出典データセット
uspto-grants-2015_03
特許番号
US08981084B2

反応ノート

読み込み中…