1-(3-Bromophenyl)propan-2-one → 5-{4-[2-(3-Bromophenyl)propyl]-1-piperazinyl)-2-methylquinoline

HRID 15843Notes

Reaction equation

HRID 15843 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](=O)C)[CH:5]=[CH:6][CH:7]=1.[CH3:12][C:13]1[CH:22]=[CH:21][C:20]2C(=[CH:16][CH:17]=[CH:18][C:19]=2[N:23]2[CH2:28][CH2:27][N:26]([CH2:29]CC3C=C(C=CC=3)N)[CH2:25][CH2:24]2)N=1.[C:38]([BH3-])#[N:39].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:9])[CH2:29][N:26]2[CH2:27][CH2:28][N:23]([C:19]3[CH:18]=[CH:17][CH:16]=[C:38]4[C:20]=3[CH:21]=[CH:22][C:13]([CH3:12])=[N:39]4)[CH2:24][CH2:25]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 27340931-(3-Bromophenyl)propan-2-oneHCID 5003444Sodium cyanoborohydrideHCID 498521053-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

Product 1

HCID 574443285-{4-[2-(3-Bromophenyl)propyl]-1-piperazinyl)-2-methylquinolineYield 50%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

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).

Workup

  1. stirringThe resulting white mixture was stirred at room temperature until hplc
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additiondiluted with aqueous sodium hydroxide solution (1M)
  4. extractionextracted with DCM
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-0e4db506b4a34fef99d9172f3bc427fc
Source dataset
uspto-grants-2010_06
Patent number
US07732600B2

Reaction notes

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