Ammonia → 1-{4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butyl}-3,4-dihydroquinolin-2(1H)-one

HRID 1791175Notes

Reaction equation

HRID 1791175 reaction equation
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.N.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][C:29]1=[O:38]>CC(=O)CC.C(OCC)(=O)C>[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:24][CH2:25][CH2:26][CH2:27][N:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30][C:29]2=[O:38])[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 129923681-(4-Bromobutan-1-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 119529191-{4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butyl}-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The free base of 1-(2,3-dichlorophenyl)piperazine, hydrochloride (6.0 g) was liberated by the use ethyl acetate and aqueous ammonia. The remaining oil was dissolved in butanone (500 mL) followed by the addition of potassium carbonate (9.7 g), and the mixture was heated to reflux temperature. To this mixture was added a solution of 1-(4-bromobutyl)-3,4-dihydroquinolin-2(1H)-one (7.9 g) in butanone (150 mL), and the resulting mixture was boiled under reflux for 10 h. The mixture was filtered hot and purified by flash chromatography (eluent:ethyl acetate/triethylamine 100:4) giving the title compound which was precipitated as the hydrochloride salt (2.5 g). Mp 234–235° C. 1H NMR (DMSO-d6): 1.55–1.65 (m, 2H); 1.75–1.85 (m, 2H); 2.55 (t, 2H); 2.85–2.90 (m, 2H); 3.05–3.20 (m, 4H); 3.25 (t, 2H); 3.40 (d, 2H); 3.55 (d, 2H); 3.95 (t, 2H); 7.00 (t, 1H); 7.15 (d, 1H); 7.20–7.30 (m, 3H); 7.30–7.40 (m, 2H); 11.35 (b s). MS m/z: 432 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux temperature
  3. temperatureunder reflux for 10 h
  4. filtrationThe mixture was filtered hot
  5. custompurified by flash chromatography (eluent:ethyl acetate/triethylamine 100:4)

Sources & evidence

ORD record
ord-b5dd867193b449d4bcf48c923e1b0011
Source dataset
uspto-grants-2006_07
Patent number
US07074796B2

Reaction notes

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