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

HRID 1160119

반응식

HRID 1160119 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-acf7ac18a4634b81b708445c06452043
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816359B2

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