1-Hexanol → 8-(1-piperazinyl)Quinoline

HRID 2184854Notes

Reaction equation

HRID 2184854 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Cl.Cl[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]Cl.C(O)CCCCC.[OH-].[Na+]>ClC1C=CC=CC=1Cl>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[N:1]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 81031-HexanolHCID 113598-AminoquinolineHCID 14798Sodium HydroxideHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 118307868-(1-piperazinyl)QuinolineYield 22%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 8-aminoquinoline (1.5 g), bis-(2-chloroethyl)amine hydrochloride (2.04 g), o-dichlorobenzene (4.5 mL) and n-hexanol (0.45 mL) was stirred at reflux temperature for 5 h. After cooling to room temperature, the mixture was treated with 2 N NaOH (10 mL) and extracted with CH2Cl2 (3×20 mL). The purification was carried out by flash chromatography (CH2Cl2-2 N methanolic NH3) 97:3 to give 0.48 g (22%) of the title compound.

Workup

  1. temperatureat reflux temperature for 5 h
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. customThe purification

Sources & evidence

ORD record
ord-16d6a2bc60b64361b191e6bd130ad713
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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