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

HRID 464820Notes

Reaction equation

HRID 464820 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 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To 60 ml of anhydrous N,N-dimethylformamide were added 4.00 g of 1-(3-diethylaminopropyl)-3-aminoindazole prepared by the same method as Example 26, 8.98 g of 3-bromopropyldiethylamine hydrobromide and 7.89 g of anhydrous potassium carbonate, and the mixture was stirred for 12 hours at 80° C. After cooling the reaction mixture, the mixture was added with 80 ml of water and extracted with diethyl ether. Then the ether layer was extracted three times with 2N-hydrochloric acid. The hydrochloric acid layer was washed with diethyl ether and the pH of the layer was adjusted to 14 with potassium carbonate. The layer was extracted three times with chloroform. The chloroform layer was dried with 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 solvent to give 3.05 g of 1-(3-diethylaminopropyl)-3-(3-diethylaminopropylamino)indazole in a yield of 52%.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with diethyl ether
  3. extractionThen the ether layer was extracted three times with 2N-hydrochloric acid
  4. washThe hydrochloric acid layer was washed with diethyl ether
  5. extractionThe layer was extracted three times with chloroform
  6. dry with materialThe chloroform layer was dried with anhydrous sodium sulfate and chloroform
  7. customwas removed under reduced pressure
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-62b0ae6c60cd4d9db919324b236cf652
Source dataset
uspto-grants-1985_10
Patent number
US04549023

Reaction notes

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