Benzenamine, 3-bromo-4-methyl- → N-(3-bromo-4-methyl-phenyl)4-(4-methyl-piperazin-1-ylmethyl)-benzamide

HRID 273289

반응식

HRID 273289 반응식
C[Al](C)C.[Br:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[CH3:13])[NH2:9].C[O:15][C:16](=O)[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[CH3:13][C:12]1[CH:11]=[CH:10][C:8]([NH:9][C:16](=[O:15])[C:17]2[CH:18]=[CH:19][C:20]([CH2:23][N:24]3[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]3)=[CH:21][CH:22]=2)=[CH:7][C:6]=1[Br:5]

참가 물질

5

반응물 3

HCID 82187Benzenamine, 3-bromo-4-methyl-HCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoateHCID 16682925Trimethylaluminum

생성물 1

HCID 10309714N-(3-bromo-4-methyl-phenyl)4-(4-methyl-piperazin-1-ylmethyl)-benzamide

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

A solution of trimethylaluminium (2M in toluene, 15.0 ml) is added over a period of 30 min to a solution of 3-bromo-4-methyl-aniline(2.15 g, 11.5 mmol) and 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid methyl ester (2.87 g, 11.5 mmol) in toluene (20 ml) at 40° C. under an atmosphere of argon. After gas evolution ceases, the reaction mixture is stirred 30 min before being cooled to 0° C. and partitioned between cold aqueous 1N NaOH (100 ml) and toluene (100 ml). The organic layer is extracted with aqueous saturated NH4Cl (100 ml) and aqueous saturated NaCl (100 ml) The organic layer is concentrated in vacuo to give 4.69 g (97 area % by HPLC) of the title compound as pale yellow crystals.

후처리

  1. custompartitioned between cold aqueous 1N NaOH (100 ml) and toluene (100 ml)
  2. extractionThe organic layer is extracted with aqueous saturated NH4Cl (100 ml) and aqueous saturated NaCl (100 ml) The organic layer
  3. concentrationis concentrated in vacuo

출처 및 근거

ORD 기록
ord-a96d00eed30545c5bcbe3c64f9b42c98
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456283B2

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