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

HRID 1170053Notes

Reaction equation

HRID 1170053 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a5bd5235cc8c42c7ae771bfef2572696
Source dataset
uspto-grants-2010_11
Patent number
US07825247B2

Reaction notes

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