1,2-Dimethoxyethane → 4-[(1H-Indol-3-yl)methyl]piperazin-1-amine

HRID 1973403Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].COCCOC.[N:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)[CH2:17][CH2:16]1)=O>O>[NH2:13][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred mixture of 10.5 g of lithium aluminum hydride in 100 ml. of 1,2-dimethoxyethane is added slowly 38 g (0.16 mol) of 3-(4-nitrosopiperazin-1-yl) methylindole while maintaining the temperature below 35° C. After total addition of the material, the mixture is refluxed for four hours. The reaction mixture is cooled to 0° C. and a solution of 50 ml. of water and 50 ml. of 1,2-dimethoxyethane is added slowly maintaining the temperature below 20° C. and an additional 50 ml. of water is added. The mixture is filtered and the solvent is removed from the filtrate. The residual solid is recrystallized from ethanol and water (2:1) to produce pure flakes of 3-(4-aminopiperazin-1-yl) methylindole, m.p. 147°-149° C. Analysis: Calculated for C13H18N4 :67.80% C; 7.88% H; 24.33% N Found: 67.69% C; 7.94% H; 24.28% N.

Workup

temperaturewhile maintaining the temperature below 35° C
additionAfter total addition of the material
temperaturethe mixture is refluxed for four hours
temperaturemaintaining the temperature below 20° C.
filtrationThe mixture is filtered
customthe solvent is removed from the filtrate
customThe residual solid is recrystallized from ethanol and water (2:1)

Sources & evidence

ORD record: ord-aa97f4a133774f22a20a9ad824fad239
Source dataset: uspto-grants-1976_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03997539

Reaction notes

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