1-Methylpiperazine → HCID 54052661, compound

HRID 1607506Notes

Reaction equation

HRID 1607506 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[CH:16]=[CH:15][C:14](=[CH:17][C:18]#[N:19])[CH2:13][C:7]32[CH2:11][N:10]([CH3:12])[CH2:9][C:8]=13.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CN(C)C=O>[C:18]([CH:17]=[C:14]1[CH2:13][C:7]23[CH2:11][N:10]([CH3:12])[CH2:9][C:8]2=[C:2]([N:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]2)[CH:3]=[CH:4][N:5]=[C:6]3[CH:16]=[CH:15]1)#[N:19]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 53844648HCID 53844648, compound

Product 1

HCID 54052661HCID 54052661, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

5.8 g (22 mmol) of 4-chloro-10-cyanomethylene-2-methylpyrrolo[4,3-e]benzazepine were dissolved in 50 ml of dimethylformamide, 6.6 ml (60 mmol) of N-methylpiperazine were added (strongly exothermic reaction) and the mixture was stirred at 80° C. under nitrogen for 1 h. After removal of the solvent under reduced pressure the residue was taken up in about 200 ml of ice/water, the mixture was make alkaline with a little 10% strength sodium hydroxide solution and then stirred while cooling for 1 h and the pale brown crude product was filtered off with suction, washing copiously with water. The crude product was purified by column chromatography (silica gel, mobile phase 95/5 methylene chloride/methanol). 5.3 g (73%) of yellowish 10-cyanomethylene-2-methyl-4-(4-methyl-1-piperazinyl)pyrrolo-[4,3-e]benzazepine were obtained in the form of a mixture of the (E) and (Z) isomers, which was recrystallized from isopropanol: melting point 178°-180° C.

Workup

  1. customstrongly exothermic reaction) and the mixture
  2. customAfter removal of the solvent under reduced pressure the residue
  3. stirringstirred
  4. temperaturewhile cooling for 1 h
  5. filtrationthe pale brown crude product was filtered off with suction
  6. washwashing copiously with water
  7. customThe crude product was purified by column chromatography (silica gel, mobile phase 95/5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-c1378bad08e5463fa679463d42010d91
Source dataset
uspto-grants-1989_09
Patent number
US04866057

Reaction notes

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