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

HRID 58168

반응식

HRID 58168 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178460666HCID 178460666, 화합물촉매HCID 887Methanol용매2회HCID 8857Ethyl Acetate용매

실험 절차

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]+

후처리

  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

출처 및 근거

ORD 기록
ord-09b9e11eaef04abeafbfb647896bb2e2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434697B2

연결된 노트

불러오는 중…