Dimethylformamide → 1H-Indazol-3-amine, N-(2-(1-piperidinyl)ethyl)-

HRID 1381306Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.Br.Br[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(Cl)(Cl)Cl.O>[N:15]1([CH2:14][CH2:13][NH:1][C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4][N:3]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

4.0 g of 3-aminoindazole prepared by the method described in C. E. KWARTLER et. al., J. Am. Chem. Soc., 65, 1804 (1943), 8.18 g of 1-(2-bromoethyl)piperidine hydrobromide obtained from Referential Example 1, 8.28 g of anhydrous potassium carbonate and 80 ml of dried N,N-dimethylformamide were mixed and stirred for 24 hours at 80° C. After the reaction mixture was condensed under reduced pressure, 100 ml of chloroform and 50 ml of water were added to the condensed residue. Then the chloroform layer was separated, dried with anhydrous sodium sulfate and chloroform was removed under reduced pressure. The residue thus obtained was subjected to alumina-column chromatography (alumina: 200 g) using chloroform as the solvent to give 4.09 g of 3-(2-piperidinoethylamino)indazole in a yield of 56%.

Workup

additionwere mixed
additionwere added to the condensed residue
customThen the chloroform layer was separated
dry with materialdried with anhydrous sodium sulfate and chloroform
customwas removed under reduced pressure
customThe residue thus obtained

Sources & evidence

ORD record: ord-bb2e4639577d43e59871f75f0f398574
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04585869

Reaction notes

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