1,2-Dimethoxyethane → HCID 12392200, compound

HRID 1973400Notes

Reaction equation

HRID 1973400 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].COCCOC.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22](=O)[C:23]([N:25]2[CH2:30][CH2:29][N:28]([N:31]=O)[CH2:27][CH2:26]2)=O)=[CH:14]1>O>[NH2:31][N:28]1[CH2:29][CH2:30][N:25]([CH2:23][CH2:22][C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:13][CH:14]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 80711,2-Dimethoxyethane2×HCID 12392195HCID 12392195, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12392200HCID 12392200, 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 (0.037 mol) of 1-(indol-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, and the mixture is then filtered. The solvent is removed from the filtrate and the residual solid is recrystallized from benzene, producing the pure crystals of 3-[2-(4-aminopiperazin-1-yl)ethyl]indole, m.p. 115°-117° C. Analysis: Calculated for C14H20N4 :68.82% C; 8.25% H; 22.93% N Found:68.70% C; 8.17% H; 22.55% 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 from the filtrate
  8. customthe residual solid is recrystallized from benzene

Sources & evidence

ORD record
ord-c5c7f99f8f394e7eb935d5fdfe19a1d1
Source dataset
uspto-grants-1976_12
Patent number
US03997539

Reaction notes

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