Triethylamine → 4-(4-Fluorophenyl)-piperazine-1-carboxylic acid 4-nitrophenyl ester

HRID 2262470ノート

反応式

HRID 2262470 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:23]>C1COCC1>[N+:31]([C:28]1[CH:27]=[CH:26][C:25]([O:24][C:22]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)=[O:23])=[CH:30][CH:29]=1)([O-:33])=[O:32]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 821294-Nitrophenyl chloroformate

生成物 1

HCID 595944824-(4-Fluorophenyl)-piperazine-1-carboxylic acid 4-nitrophenyl ester収率 67.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

1-(4-Fluoro-phenyl)-piperazine (12.2 g, 67.7 mmol) and triethylamine (4.63 mL, 67.7 mmol) were dissolved in anhydrous THF (150 mL) under nitrogen and the reaction mixture was cooled to 0° C. 4-Nitrophenyl chloroformate (13.4 g, 67.7 mmol) dissolved in anhydrous THF (150 mL) at 0° C. was added and the reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue suspended between water and EtOAc. The aqueous layer was extracted with two further portions of EtOAc, the organic layers were combined, dried (MgSO4), dried in vacuo and then recrystallised from toluene (50 mL)/hexane (60 mL) to give 4-(4-fluorophenyl)-piperazine-1-carboxylic acid 4-nitrophenyl ester (15.8 g, 67%) as fine yellow needles.

後処理

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. extractionThe aqueous layer was extracted with two further portions of EtOAc
  4. dry with materialdried (MgSO4)
  5. customdried in vacuo
  6. customrecrystallised from toluene (50 mL)/hexane (60 mL)

出典と根拠

ORDレコード
ord-97e67a0b8d264d1c9a18424c2126d1a0
出典データセット
uspto-grants-2010_12
特許番号
US07851471B2

反応ノート

読み込み中…