1-Methylpiperazine → HCID 11087453, compound

HRID 392762Notes

Reaction equation

HRID 392762 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([OH:15])=O)=[CH:7]2)([O-:3])=[O:2].Cl.CN(C)CCCN=C=NCC.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>ClCCl>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:13]([C:8]2[NH:9][C:10]3[C:6]([CH:7]=2)=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)=[O:15])[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 3512915-Nitroindole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 11087453HCID 11087453, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5-nitroindole-2-carboxylic acid (4.38 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 4.89 g) in dichloromethane (150 mL) was treated with N-methylpiperazine (2.83 mL) and stirred at ambient temperature for 16 h. The reaction mixture was poured into dichloromethane (200 mL), washed with water, saturated sodium hydrogencarbonate solution and then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via silica gel chromatography (0-10% 2 M ammonia in methanol/dichloromethane) to give the title compound (1.8 g). 1H NMR (400 MHz, CDCl3): δ 10.97 (br s, 1H), 8.58 (d, J=2.15 Hz, 1H), 8.11 (dd, J=2.15, 7.04 Hz, 1H), 7.44 (d, J=9.00 Hz, 1H), 6.89 (s, 1H), 3.95 (br m, 4H), 2.52 (t, J=4.89 Hz, 4H), 2.34 (s, 3H). MS (electrospray): exact mass calculated for C14H16N4O3, 288.12; m/z found, 289.1 [M+H]+.

Workup

  1. washwashed with water, saturated sodium hydrogencarbonate solution
  2. dry with materialbrine, dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified via silica gel chromatography (0-10% 2 M ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-173ef10d1e8d431d9ec3bd9ea5599a81
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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