Water → 3-Butyryl-4-(2-methylphenylamino)-8-(3-piperidinopropoxy)quinoline

HRID 1090661Notes

Reaction equation

HRID 1090661 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[OH:24])(=[O:5])[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].Cl.Cl[CH2:33][CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.O>CN(C)C=O>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:24][CH2:33][CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 104037323-Butyryl-4-(2-methylphenylamino)8-hydroxyquinolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 99809633-Butyryl-4-(2-methylphenylamino)-8-(3-piperidinopropoxy)quinolineYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Butyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (3.2 g, 10 mmol) and potassium t-butoxide (5.0 g, 40 mmol) were dissolved in dry dimethylformamide (100 ml) at 80° , then 1-(3-chloropropyl)piperidine hydrochloride (4.0 g, 20 mmol) added and stirred for I hour. The mixture was poured into water, extracted with ether, and the extracts dried and evaporated. Chromatography (silica gel, 3-5% methanolic ammonia in dichloromethane) and recrystallisation from ether/petroleum ether gave 3-butyryl-4-(2-methylphenylamino)-8-(3-piperidinopropoxy)quinoline (1.2 g, 27%), m.p. 76°-78°.

Workup

  1. extractionextracted with ether
  2. customthe extracts dried
  3. customevaporated
  4. customChromatography (silica gel, 3-5% methanolic ammonia in dichloromethane) and recrystallisation from ether/petroleum ether

Sources & evidence

ORD record
ord-349507129ca84ae9ac3b34d38d68f57a
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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