Reaction #44121

Reaction equation

1-(3-bromophenyl)-2-propanone

2-methyl-5-(1-piperazinyl)quinoline

3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

sodium cyanoborohydride

→

title compound

Yield 50.0%

5-{4-[2-(3-bromophenyl)propyl]-1-piperazinyl}-2-methylquinoline

Yield 50.0%

Solvents

methanol

Conditions

Workup

1. 1
   workup.STIRRINGThe resulting white mixture was stirred at room temperature until hplc
2. 2
   ConcentrationThe mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with aqueous sodium hydroxide solution (1M)
4. 4
   Extractionextracted with DCM
5. 5
   WashThe combined organic phases were washed with brine
6. 6
   Dryingdried over sodium sulfate
7. 7
   Concentrationconcentrated
8. 8
   OtherThe crude was purified by chromatography

Procedure

A solution of zinc(II) chloride (0.5 M, THF, 0.5 eq., 234 uL) was added to a stirred solution of 1-(3-bromophenyl)-2-propanone (50 mg) and 2-methyl-5-(1-piperazinyl)quinoline (D3) (2.0 eq., 107 mg) in methanol (1 ml). The mixture was stirred 10 minutes then a solution of sodium cyanoborohydride (1M, THF, 1.0 eq., 234 uL) was added. The resulting white mixture was stirred at room temperature until hplc showed the complete disappearance of starting material. The mixture was concentrated under reduced pressure, diluted with aqueous sodium hydroxide solution (1M), and extracted with DCM. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The crude was purified by chromatography using a SPE cartridge (SiO2) with DCM-methanol (98:2) as eluent to afford the title compound (50 mg, 50% yield).

Source