1-Methylpiperazine → HCID 68568419, compound

HRID 220619Notes

Reaction equation

HRID 220619 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH2:16]Br)=[O:5].[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C1COCC1>[CH2:2]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH2:16][N:29]1[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]1)=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 67414524HCID 67414524, compound

Product 1

HCID 68568419HCID 68568419, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 0.125 g (0.30 mmol) of 7-bromomethyl-5-chloro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in THF (1 ml) at RT, 55 mg of 1-methyl-piperazine was added. The reaction mixture was stirred at 40° C. for one hour and concentrated under vacuo. The crude was dissolved in CH2Cl2 (1 m) and at RT 0.2 ml of TFA was added and stirring was continued over night. Preparative HPLC (30% CH3CN/H2O) afforded 30 mg (29%) of 5-chloro-7-(4-methyl-piperazin-1-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester as colorless oil.

Workup

  1. concentrationconcentrated under vacuo
  2. dissolutionThe crude was dissolved in CH2Cl2 (1 m) and at RT 0.2 ml of TFA
  3. additionwas added
  4. stirringstirring
  5. waitwas continued over night

Sources & evidence

ORD record
ord-54216294e9e644d79153343ab89dacf2
Source dataset
uspto-grants-2012_06
Patent number
US08202993B2

Reaction notes

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