1-Methylpiperazine → 4-Methyl-piperazine-1-carboxylic acid methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amide

HRID 646878ノート

反応式

HRID 646878 の反応式
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[CH3:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:16]=1.CCN(C(C)C)C(C)C.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:13][N:14]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:16]=1)[C:5]([N:43]1[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]1)=[O:11]

参加物

7

反応物 4

HCID 531671-MethylpiperazineHCID 81531Diisopropylethylamine2 回HCID 94429TriphosgeneHCID 68680582N-methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine

生成物 1

HCID 686800824-Methyl-piperazine-1-carboxylic acid methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amide収率 86%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

To a solution of triphosgene (40.6 mg, 0.13 mmol) in 2 mL of CH2Cl2 was added methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine (88 mg, 0.37 mmol) and DIEA (38 μL, 0.22 mmol) in 2 mL of CH2Cl2 over a 15 min. period. A solution of N-methylpiperazine (1.2 eq, 41 μL) and DIEA (38 μL, 0.22 mmol) in 1.5 mL of CH2Cl2 were then added via cannula and stirring was continued for 10 min. The reaction was diluted with CHCl3 (50 mL) and washed with satd aq NaHCO3 (50 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to give 115 mg (86%) of the title compound a yellow oil. Mass spectrum (ESI, m/z): Calcd. for C18H27N5O3, 362.2 (M+H), found 362.2.

後処理

  1. washwashed with satd aq NaHCO3 (50 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-be62f9a6e6b44a6cafaf1c26c25b354d
出典データセット
uspto-grants-2010_04
特許番号
US07705042B2

反応ノート

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