1-Methylpiperazine → 2-Chloro-N-methyl-4-(4-methyl-piperazin-1-yl)-benzamide

HRID 1267519Notes

Reaction equation

HRID 1267519 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](F)[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>>[Cl:1][C:2]1[CH:11]=[C:10]([N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 531671-Methylpiperazine2×HCID 171445352-chloro-4-fluoro-N-methylbenzamide

Product 1

HCID 185465032-Chloro-N-methyl-4-(4-methyl-piperazin-1-yl)-benzamideYield 52.5%

Procedure

A mixture of 316 mg (1.68 mmol) 2-chloro-4-fluoro-N-methyl-benzamide and 0.94 ml (8.4 mmol) 1-methylpiperazine was heated at 140° for 7 h in a sealed glass tube. After cooling to room temperature excess 1-methylpiperazine was removed by distillation at 50°/0.5 mbar. The residue was partitioned between 25 ml CH2Cl2/2 N NaOH solution. The layers were separated and the aqueous layer was extracted with 3 15-ml portions of dichloromethane. The combined organic extracts were dried (Na2SO4) and evaporated. Chromatography (SiO2, CH2Cl2/methanol 19:1) yielded 236 mg (52%) 2-Chloro-N-methyl-4-(4-methyl-piperazin-1-yl)-benzamide as a light yellow solid, MS (EI): 267 (M+).

Workup

  1. temperaturewas heated at 140° for 7 h in a sealed glass tube
  2. customwas removed by distillation at 50°/0.5 mbar
  3. customThe residue was partitioned between 25 ml CH2Cl2/2 N NaOH solution
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with 3 15-ml portions of dichloromethane
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-8e176263995a49bfb7a69150c243181a
Source dataset
uspto-grants-2003_04
Patent number
US06552088B2

Reaction notes

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