Hydrazine hydrate (1:1) → Piperazine,1-(1h-indol-5-ylcarbonyl)-4-methyl-

HRID 1260369Notes

Reaction equation

HRID 1260369 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([N+]([O-])=O)=[C:12]([CH:19]=[CH:20][N:21]3CCCC3)[CH:11]=2)=[O:9])[CH2:4][CH2:3]1.O.NN>[Ni].C1COCC1>[NH:21]1[C:13]2[C:12](=[CH:11][C:10]([C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)=[O:9])=[CH:15][CH:14]=2)[CH:19]=[CH:20]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86639102HCID 86639102, compound

Product 1

HCID 63719141Piperazine,1-(1h-indol-5-ylcarbonyl)-4-methyl-

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

(4-Methylpiperazin-1-yl)-[4-nitro-3-(2-pyrrolidin-1-yl-vinyl)phenyl]methanone (2.907 mmol, 1.0 gram) (obtained from step (ii)) was taken in a 25 mL, two necked round bottom flask provided with a condenser, under nitrogen atmosphere. To this THF (7 mL) was added, followed by Raney-Nickel (Ra-Ni) (0.1 gram). Hydrazine hydrate (14.54 mmol, 0.73 gram) was added to the above reaction mixture in such a way that the reaction mixture starts refluxing. The reaction mixture was further refluxed for 3 hours. After the completion of reaction, Ra-Ni was removed by filtration, THF and methanol were distilled off and the concentrate was diluted with water (20 mL), basified with 20% sodium hydroxide solution to pH: 10 and the mixture was extracted with ethyl acetate (2×30 mL). The combined ethyl acetate extracts were then washed with water (2×30 mL), brine (30 Ml) and dried over anhydrous sodium sulfate. The volatiles were removed under the reduced pressure to obtain thick syrupy mass. This thick syrupy mass was purified over silica gel column, eluent being ethyl acetate and triethylamine (0.2 to 1.0%).

Workup

  1. customprovided with a condenser, under nitrogen atmosphere
  2. temperaturestarts refluxing
  3. temperatureThe reaction mixture was further refluxed for 3 hours
  4. customwas removed by filtration, THF and methanol
  5. distillationwere distilled off
  6. additionthe concentrate was diluted with water (20 mL)
  7. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  8. washThe combined ethyl acetate extracts were then washed with water (2×30 mL), brine (30 Ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe volatiles were removed under the reduced pressure
  11. customto obtain thick syrupy mass
  12. customThis thick syrupy mass was purified over silica gel column, eluent

Sources & evidence

ORD record
ord-81080c4fc85b4c1b9e6fc3b3fd7ae58c
Source dataset
uspto-grants-2013_06
Patent number
US08470830B2

Reaction notes

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