1-Ethylpiperazine → 4-(4-Ethyl-piperazin-1-ylmethyl)-2-nitro-phenylamine

HRID 58168

反応式

HRID 58168 の反応式
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].[NH2:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19].[BH4-].[Na+]>CO.CCOC(C)=O.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:14][C:13]2[CH:16]=[CH:17][C:10]([NH2:9])=[C:11]([N+:18]([O-:20])=[O:19])[CH:12]=2)[CH2:5][CH2:4]1)[CH3:2]

参加物

7

反応物 3

HCID 791961-EthylpiperazineHCID 4311764Sodium borohydrideHCID 132377034-Amino-3-nitrobenzaldehyde

生成物 1

HCID 550463954-(4-Ethyl-piperazin-1-ylmethyl)-2-nitro-phenylamine収率 34%

試薬・触媒・溶媒 3

HCID 178460666HCID 178460666、化合物触媒HCID 887Methanol溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 1-ethyl-piperazine (1.37 g, 12 mmol) in MeOH (30 mL) was added Ti(OiPr)4 (1.73 g, 6 mmol). Then the solution was stirred at room temperature for 15 min. Then 4-amino-3-nitro-benzaldehyde (Procedure 2F, steps a-b, 1.5 g, 9 mmol) in MeOH (10 mL) was added and the solution was stirred at room temperature overnight. Then NaBH4 (380 mg, 10 mmol) was added and the solution was stirred at room temperature for 1 hour. The solution was diluted with EtOAc and filtered. The filtrate was washed with water and brine, dried over anhydrous Na2SO4. Concentration gave product, which was purified by flash chromatography on silica to obtain the title compound (800 mg, yield: 34%). MS (ESI): 265 [M+H]+

後処理

  1. stirringthe solution was stirred at room temperature overnight
  2. stirringthe solution was stirred at room temperature for 1 hour
  3. filtrationfiltered
  4. washThe filtrate was washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationConcentration
  7. customgave product, which
  8. customwas purified by flash chromatography on silica

出典と根拠

ORDレコード
ord-09b9e11eaef04abeafbfb647896bb2e2
出典データセット
uspto-grants-2016_09
特許番号
US09434697B2

関連ノート

読み込み中…