4-Methyl-3-nitroaniline → N-(4-Methyl-3-nitro-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide

HRID 273291

반응식

HRID 273291 반응식
C[Al](C)C.[N+:5]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][C:14]=1[CH3:15])[NH2:11])([O-:7])=[O:6].C[O:17][C:18](=O)[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)=[CH:21][CH:20]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(Cl)Cl.COC(C)(C)C>[CH3:15][C:14]1[CH:13]=[CH:12][C:10]([NH:11][C:18](=[O:17])[C:19]2[CH:20]=[CH:21][C:22]([CH2:25][N:26]3[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]3)=[CH:23][CH:24]=2)=[CH:9][C:8]=1[N+:5]([O-:7])=[O:6]

참가 물질

8

반응물 4

HCID 83904-Methyl-3-nitroanilineHCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoateHCID 9855836Potassium sodium tartarateHCID 16682925Trimethylaluminum

생성물 1

HCID 29984087N-(4-Methyl-3-nitro-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6344Dichloromethane용매HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
0 °C

실험 절차

A solution of trimethylaluminium (2M in toluene, 1.3 ml, 2.6 mmol) is added over a period of 5 min to a solution of 3-nitro-4-methyl-aniline(152 mg, 1.00 mmol) and 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid methyl ester (248 mg, 1.00 mmol) in toluene (3.0 ml) at 45° C. under an atmosphere of argon. After gas evolution ceases, the dark brown reaction mixture is stirred 30 min before being cooled to 0° C. An aqueous saturated solution of potassium-sodium tartrate (20 ml), t-butyl methyl ether (15 ml) and methylene chloride (10 ml) are added sequentially. The organic phase is separated and washed with aqueous saturated NaHCO3 (10 ml) and aqueous saturated NaCl (10 ml). The aqueous phases are back-extracted with t-butyl methyl ether (2×15 ml). The organic phases are combined, dried over MgSO4 and concentrated in vacuo to give 383 mg (96 area % by HPLC) of the title compound as pale yellow crystals.

후처리

  1. customThe organic phase is separated
  2. washwashed with aqueous saturated NaHCO3 (10 ml) and aqueous saturated NaCl (10 ml)
  3. extractionThe aqueous phases are back-extracted with t-butyl methyl ether (2×15 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e01e68b5d0e6410ebe169c13eb7d4d6c
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456283B2

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