Triethylamine → Tert-butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylate

HRID 2209167ノート

反応式

HRID 2209167 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(CC)CC)C>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:14]2[CH2:13][CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[C:6]([C:7]#[N:8])[CH:9]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27249005-Bromo-2-fluorobenzonitrile

生成物 1

HCID 56763808Tert-butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylate収率 80%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

In a pressure tube, 5-bromo-2-fluorobenzonitrile (2500 mg, 12.5 mmol), tert-butyl piperazine-1-carboxylate (2444.45 mg, 13.12 mmol), triethylamine (5.23 ml, 37.5 mmol) in dimethylsulfoxide (10 ml) were combined and refluxed at 100 C for ovn. The mixture was cooled, and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was dried using sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel 5-60% ethyl acetate/hexane to provide a light brown oil, tert-butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylate (3660 mg, 80%).

後処理

  1. temperaturerefluxed at 100 C for ovn
  2. temperatureThe mixture was cooled
  3. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel 5-60% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-f7aeb9dea80e4af889c73bab9a226e2c
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

反応ノート

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