Dimethylformamide → 1-(3-Piperidinopropyl)-3-(3-diethylaminopropylamino)-5-chloroindazole

HRID 580155Notes

Reaction equation

HRID 580155 reaction equation
CN(C)C=O.[N:6]1([CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[C:17]([NH2:25])=[N:16]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.Br.Br[CH2:28][CH2:29][CH2:30][N:31]([CH2:34][CH3:35])[CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[N:6]1([CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[C:17]([NH:25][CH2:28][CH2:29][CH2:30][N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[N:16]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12639158(3-Bromopropyl)diethylamine hydrobromideHCID 201357951-(3-Piperidinopropyl)-3-amino-5-chloroindazole

Product 1

HCID 201357691-(3-Piperidinopropyl)-3-(3-diethylaminopropylamino)-5-chloroindazoleYield 54.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To 60 ml of anhydrous N,N-dimethylformamide were added 9.59 g of 1-(3-piperidinopropyl)-3-amino-5-chloroindazole, 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 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 7.18 g of 1-(3-piperidinopropyl)-3-(3-diethylaminopropylamino)-5-chloroindazole having the following analytical values in a yield of 54%.

Workup

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

Sources & evidence

ORD record
ord-bd9bac63ef144308bfd435ca34cbf99a
Source dataset
uspto-grants-1988_06
Patent number
US04751302

Reaction notes

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