Dimethylformamide → 1,3-Propanediamine, N,N-diethyl-N'-(1H-indazol-3-yi)-

HRID 484860Notes

Reaction equation

CN(C)C=O.[NH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][N:8]=1.Br.Br[CH2:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[CH2:22]([N:21]([CH2:24][CH3:25])[CH2:20][CH2:19][CH2:18][NH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][N:8]=1)[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To 80 ml of anhydrous N,N-dimethylformamide were added 5.0 g of 3-aminoindazole, 8.30 g of 3-bromopropyldiethylamine hydrobromide and 8.3 g of anhydrous potassium carbonate. The mixture was stirred for 24 hours at 80° C. and condensed under reduced pressure. The condensed residue was added with 100 ml of chloroform and 50 ml of water. 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 development solvent to give 4.81 g of 3-(3-diethylaminopropylamino)indazole having the following analytical values in a yield of 52%.

Workup

customcondensed under reduced pressure
dry with materialThe chloroform layer was dried over anhydrous sodium sulfate, and chloroform
customwas removed under reduced pressure
customThe residue thus obtained

Sources & evidence

ORD record: ord-e6d7a866ce4f457aa5537182e8d0f704
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04533731

Reaction notes

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