1,2-Dimethoxyethane → HCID 12392201, compound

HRID 1973401Notes

Reaction equation

HRID 1973401 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].COCCOC.[CH3:13][C:14]1[NH:15][C:16]2[C:21]([C:22]=1[C:23](=O)[C:24]([N:26]1[CH2:31][CH2:30][N:29]([N:32]=O)[CH2:28][CH2:27]1)=O)=[CH:20][CH:19]=[CH:18][CH:17]=2>O>[NH2:32][N:29]1[CH2:30][CH2:31][N:26]([CH2:24][CH2:23][C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]=2[CH3:13])[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 80711,2-Dimethoxyethane2×HCID 12392197HCID 12392197, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12392201HCID 12392201, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-5 °C

Procedure

To a stirred mixture of 9.0 g of lithium aluminum hydride in 400 ml. of 1,2-dimethoxyethane is added 10.52 g (0.35 mol) of 1-(2-methylindol-3-ylglyoxyloyl)-4-nitrosopiperazine slowly to maintain reaction temperature below 35° C. After all the material is added, the mixture is refluxed for 14-16 hours. The reaction mixture is cooled to -5° C. and a solution of 50 ml. of water and 50 ml. of 1,2-dimethoxyethane is slowly added while maintaining the temperature below 15° C. Another 50 ml. of water is added. The mixture is then filtered, the solvent is removed, and the residual solid is recrystallized from hot benzene, producing the pure crystals of 3-[2-(4-aminopiperazin-1-yl)ethyl]-2-methylindole, m.p. 118°-120° C. Analysis: Calculated for C15H22N4 : 71.08% C; 8.21% H; 20.72% N Found:71.11% C; 8.28% H; 20.75 % N.

Workup

  1. temperatureto maintain
  2. customreaction temperature below 35° C
  3. additionAfter all the material is added
  4. temperaturethe mixture is refluxed for 14-16 hours
  5. temperaturewhile maintaining the temperature below 15° C
  6. filtrationThe mixture is then filtered
  7. customthe solvent is removed
  8. customthe residual solid is recrystallized from hot benzene

Sources & evidence

ORD record
ord-5a35ccab75634d1c8b94d1c4ce207321
Source dataset
uspto-grants-1976_12
Patent number
US03997539

Reaction notes

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