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

HRID 2105914Notes

Reaction equation

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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-5a72adc4eb30425db7b6b91e7310affd
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579467B2

Reaction notes

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