1-Methylpiperazine → HCID 11065080, compound

HRID 392763Notes

Reaction equation

HRID 392763 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([OH:13])=O)=[CH:7]2.Cl.CN(C)CCCN=C=NCC.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([N:30]1[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]1)=[O:13])=[CH:7]2

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 32961197-methyl-1H-indole-2-carboxylic acid

Product 1

HCID 11065080HCID 11065080, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-methylindole-2-carboxylic acid (1.79 g, 10 mmol),1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 2.88 g, 15 mmol) in CH2Cl2 (100 mL) was treated with N-methylpiperazine (2.22 mL, 20 mmol). The reaction mixture was stirred at ambient temperature for 16 h and then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (100 mL), washed with water (25 mL×2) and then brine (25 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. This product was purified via silica gel chromatography (5-10% methanol/dichloromethane) to give the title compound as a white solid (2.5 g, 97.3%). 1H NMR (400 MHz, CDCl3): δ 11.07 (br s, 1H), 7.43 (d, J=7.04 Hz, 1H), 7.00-6.92 (m, 2H), 6.71 (d, J=1.96 Hz, 1H), 3.86 (br s, 4H), 2.37 (s, 3H), 2.35-2.28 (m, 4H), 2.19 (s, 3H). MS (electrospray): exact mass calculated for C15H19N3O, 257.15; m/z found, 258.2 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
  3. washwashed with water (25 mL×2)
  4. dry with materialbrine (25 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThis product was purified via silica gel chromatography (5-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-83df22dabf1647d88983e6da38314eb4
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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