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

HRID 646878노트

반응식

HRID 646878 반응식
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]

참가 물질

7

반응물 4

HCID 531671-MethylpiperazineHCID 81531Diisopropylethylamine2회HCID 94429TriphosgeneHCID 68680582N-methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매3회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-be62f9a6e6b44a6cafaf1c26c25b354d
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705042B2

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