Hydrochloric Acid → 1-[2-(4-Nitrophenyl)ethyl]-4-[2-(4-nitrophenyl)propyl]piperazine

HRID 1519568노트

반응식

HRID 1519568 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18](=O)[CH:19]([C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)[CH3:20])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[OH-].[Na+]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH:19]([C:21]3[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)[CH3:20])[CH2:16][CH2:17]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866944681-[2-(4-Nitrophenyl)ethyl]-4-[2-(4-nitrophenyl)propanoyl]piperazine

생성물 1

HCID 714510521-[2-(4-Nitrophenyl)ethyl]-4-[2-(4-nitrophenyl)propyl]piperazine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

Borane tetrahydrofuran complex 1M (0.714 ml, 0.714 mmol) was added to a stirred solution of 1-[2-(4-nitrophenyl)ethyl]-4-[2-(4-nitrophenyl)propanoyl]piperazine (92 mg, 0.22 mmol) in THF then refluxed for 1 hr. LC-MS and TLC showed starting material left. More borane-THF complex 1M (0.71 ml, 0.71 mmol) was added to the reaction and refluxed for 5 hrs. The reaction was cooled and added 6N HCl and then warmed to 65° C. for 0.5 hour. The reaction was poured into 1N NaOH and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine then dried and concentrated. The residue was purified by mass directed HPLC. LC-MS (IE, m/z): 399 [M+1]+. (0.34 μM)

후처리

  1. temperaturethen refluxed for 1 hr
  2. waitleft
  3. additionMore borane-THF complex 1M (0.71 ml, 0.71 mmol) was added to the reaction
  4. temperaturerefluxed for 5 hrs
  5. temperatureThe reaction was cooled
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with water and brine
  8. customthen dried
  9. concentrationconcentrated
  10. customThe residue was purified by mass

출처 및 근거

ORD 기록
ord-e2dc9832342146f78d5bd6801be6f079
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073882B2

반응 노트

불러오는 중…