Benzylamine → Benzyl-[4-(4-methylpiperazine-1-sulfonyl)-2-nitrophenyl]amine

HRID 241418Notes

Reaction equation

HRID 241418 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(OC)(C)C>C(O)CCC>[CH2:21]([NH:28][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 15413tert-Butyl methyl etherHCID 28424191-[(4-Chloro-3-nitrophenyl)sulfonyl]-4-methylpiperazine

Product 1

HCID 9186770Benzyl-[4-(4-methylpiperazine-1-sulfonyl)-2-nitrophenyl]amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

17.2 2.8 g (8.756 mmol) of 1-(4-chloro-3-nitrobenzenesulfonyl)-4-methylpiperazine are dissolved in 10 ml of 1-butanol, and 1.913 ml (17.5 mmol) of benzylamine are added. The reaction mixture is heated under reflux for 14 h. After cooling, MTBE is added, the precipitate formed is filtered off with suction and washed with MTBE and dried in vacuo, giving benzyl-[4-(4-methylpiperazine-1-sulfonyl)-2-nitrophenyl]amine; HPLC-MS [M+H]+ 391.2.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 14 h
  3. temperatureAfter cooling
  4. customthe precipitate formed
  5. filtrationis filtered off with suction
  6. washwashed with MTBE
  7. customdried in vacuo

Sources & evidence

ORD record
ord-0af41d8e01274460a393a3f59cb0fb95
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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