1-Methylpiperazine → HCID 21854014, compound

HRID 254190Notes

Reaction equation

HRID 254190 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.C(Cl)(=O)C(Cl)=O.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([N:23]2[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]2)=[O:12])=[CH:2]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 65578Oxalyl chlorideHCID 69867Indole-3-Carboxylic Acid

Product 1

HCID 21854014HCID 21854014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1H-Indole-3-carboxylic acid (1.61 g, 0.01 moles) was stirred with oxalyl chloride (0.99 g, 0.011 moles) in 20 mL dichloromethane at 0 to 25° C. for 3-4 hours. After completion of the reaction (TLC), volatile substances were distilled off under the reduced pressure. The residue was taken in 20 mL dichloroethane and to this stirred solution, was added N-methylpiperazine (1.1 g, 0.011 moles). The reaction mixture was further stirred for next 3-5 hours, till the reaction completes (TLC). Reaction mixture was diluted with dichloromethane 20 mL), washed with water, brine and saturated solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and the organic solvents were evaporated under vacuo. The product was purified using column chromatography on silica gel G stationary phase and suitable combinations of ethyl acetate and methanol in increasing gradient, as the mobile phase.

Workup

  1. customAfter completion of the reaction (TLC), volatile substances
  2. distillationwere distilled off under the reduced pressure
  3. customReaction mixture
  4. washwashed with water, brine and saturated solution of sodium bicarbonate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe organic solvents were evaporated under vacuo
  7. customThe product was purified
  8. temperaturein increasing gradient

Sources & evidence

ORD record
ord-cc4e0ab2ff76430bafd695424be4e25e
Source dataset
uspto-grants-2011_01
Patent number
US07875605B2

Reaction notes

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