1,4-Dibromobutane → HCID 53328349, compound

HRID 1190877Notes

Reaction equation

HRID 1190877 reaction equation
[CH3:1][C:2]1[C:3]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[C:4]([CH2:11][NH2:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:19][N:16]1[CH2:15][CH2:14][N:13]([C:3]2[C:4]([CH2:11][N:12]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[CH3:1])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 53328346HCID 53328346, compound

Product 1

HCID 53328349HCID 53328349, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of [3-methyl-2-(4-methylpiperazin-1-yl)-5-nitrophenyl]methanamine (188 mg, 0.71 mmol), 1,4-dibromobutane (93 μL, 1.1 eq) and K2CO3 (490 mg, 5 eq) in 15 mL of acetonitrile was refluxed for 48 h. After filtration and evaporation of the filtrate, the residue was purified by flash chromatography (DCM/MeOH/NH4OH//9/1/0.1) to yield expected compound as a pale yellow oil (120 mg, 53% yield).

Workup

  1. temperaturewas refluxed for 48 h
  2. filtrationAfter filtration and evaporation of the filtrate
  3. customthe residue was purified by flash chromatography (DCM/MeOH/NH4OH//9/1/0.1)

Sources & evidence

ORD record
ord-e1a89dd454f1472ea5da2158e4b75b2e
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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