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

HRID 1519568ノート

反応式

HRID 1519568 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-e2dc9832342146f78d5bd6801be6f079
出典データセット
uspto-grants-2015_07
特許番号
US09073882B2

反応ノート

読み込み中…