Dimethylformamide → 1-(3-Diethylaminopropyl)-3-(3-diethylaminopropylamino)indazole

HRID 580151Notes

Reaction equation

HRID 580151 reaction equation
CN(C)C=O.[CH2:6]([N:8]([CH2:22][CH3:23])[CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([NH2:21])=[N:13]1)[CH3:7].Br.Br[CH2:26][CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[CH2:22]([N:8]([CH2:6][CH3:7])[CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([NH:21][CH2:26][CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[N:13]1)[CH3:23]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 30288931H-Indazole-1-propanamine, 3-amino-N,N-diethyl-HCID 12639158(3-Bromopropyl)diethylamine hydrobromide

Product 1

HCID 30308371-(3-Diethylaminopropyl)-3-(3-diethylaminopropylamino)indazoleYield 59.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To 60 ml of anhydrous N,N-dimethylformamide were added 8.1 g of 1-(3-diethylaminopropyl)-3-amino-indazole obtained by the same method as described in Example 5, 9.0 g of 3-bromopropyldiethylamine hydrobromide and 7.9 g of anhydrous potassium carbonate. The mixture was stirred for 12 hours at 80° C. After cooling, the mixture was added with 80 ml of water and extracted with diethyl ether. The diethyl ether layer was extracted three times with 2N hydrochloric acid, and the hydrochloric acid layer was washed with diethyl ether. The pH of the layer was adjusted to at least 11 with potassium carbonate, and the alkali layer was extracted three times with chloroform. The chloroform layer was dried over anhydrous sodium sulfate, and chloroform was removed under reduced pressure. The residue thus obtained was subjected to an alumina-column chromatography(alumina: 200 g) using chloroform as the developing solvent to give 6.99 g of 1-(3-diethylaminopropyl)-3-(3-diethylaminopropylamino)indazole having the following analytical values in a yield of 54%.

Workup

  1. customobtained by the same method
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. extractionThe diethyl ether layer was extracted three times with 2N hydrochloric acid
  5. washthe hydrochloric acid layer was washed with diethyl ether
  6. extractionthe alkali layer was extracted three times with chloroform
  7. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate, and chloroform
  8. customwas removed under reduced pressure
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-e9f3beec70c64ef494c61964930983a8
Source dataset
uspto-grants-1988_06
Patent number
US04751302

Reaction notes

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