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Ethanol → 4-(4-Amino-2-trifluoromethyl-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl ester

HRID 1841945
ノート
印刷プレビュー

反応式

HRID 1841945 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][C:21]=2[C:29]([F:32])([F:31])[F:30])(=[O:19])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[Cl-].[NH4+]>[Fe].O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=2[C:29]([F:32])([F:30])[F:31])(=[O:19])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 569547274-(4-Nitro-2-trifluoromethyl-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl ester

生成物 1

HCID 569549454-(4-Amino-2-trifluoromethyl-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl ester収率 99.2%

試薬・触媒・溶媒 2

HCID 23925Iron触媒
HCID 962
Water
溶媒

反応条件

温度
80 °C

実験手順

4-(4-Nitro-2-trifluoromethyl-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl ester (0.5 g, 1.0 mmol) was suspended in a 5:1 mixture of ethanol and water (20 ml). To this solution was added iron powder (0.16 g, 2.6 mmol) followed by saturated ammonium chloride solution (1 ml) and the mixture was heated to 80° C. for three hours. After this time, the reaction mixture was cooled to room temperature and filtered through a pad of celite, the celite was washed with ethanol (10 ml) and ethyl acetate (50 ml) and the solution was concentrated under vacuum. The resulting residue was partitioned between DCM (50 ml) and water (20 ml), the organic layer was separated, dried with MgSO4, filtered and concentrated to afford the title compound (0.44 g, 94% yield) as a yellow solid. Tr=2.03 min, m/z (ES+) (M+H)+ 444.

後処理

  1. temperatureAfter this time, the reaction mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. washthe celite was washed with ethanol (10 ml) and ethyl acetate (50 ml)
  4. concentrationthe solution was concentrated under vacuum
  5. customThe resulting residue was partitioned between DCM (50 ml) and water (20 ml)
  6. customthe organic layer was separated
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-1c0c03978edb486abf77fb81f95bf308
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946197B2

反応ノート

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