Water → N4-cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N1-phenyl-benzene-1,4-diamine

HRID 1241934ノート

反応式

HRID 1241934 の反応式
[CH:1]1([CH2:7][NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:11](F)[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[CH:1]1([CH2:7][NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:11]([N:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]3)[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 962WaterHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 21061670N4-cyclohexylmethyl-2-fluoro-5-nitro-N1-phenyl-benzene-1,4-diamine

生成物 1

HCID 21061669N4-cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N1-phenyl-benzene-1,4-diamine収率 80.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of N4-cyclohexylmethyl-2-fluoro-5-nitro-N1-phenyl-benzene-1,4-diamine (0.23 g, 0.66 mmol), N-methylpiperazine (0.22 mL, 1.97 mmol) and N,N′-diisopropylethylamine (0.34, 1.97 mmol) in DMF (3.0 mL) was stirred at 100° C. under an inert atmosphere for 16 h. The reaction mixture was transferred to a separatory funnel containing water. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, brine and dried over MgSO4. The solution was filtered through diatomaceous earth and the solvent was evaporated. The resulting dark red residue was flash chromatographed (5% MeOH/CH2Cl2) to give N4-cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N1-phenyl-benzene-1,4-diamine as a red foam (0.22 g, 80.7% yield). M+, 424

後処理

  1. customThe reaction mixture was transferred to a separatory funnel
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered through diatomaceous earth
  6. customthe solvent was evaporated
  7. customchromatographed (5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-01af52ea6a9b4085a881b35077b3bda5
出典データセット
uspto-grants-2006_10
特許番号
US07115644B2

反応ノート

読み込み中…