Sodium Hydroxide → HCID 59293687, compound

HRID 1430162Notes

Reaction equation

HRID 1430162 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)([CH3:12])[CH3:11])[CH:5]=1.Cl.[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25]Cl>CN(C=O)C.CCOC(C)=O.O>[Br:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:25][CH2:24][CH2:23][N:22]([CH3:27])[CH3:21])=[CH:17][CH:18]=2)([CH3:11])[CH3:12])[CH:5]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 57417096HCID 57417096, compound

Product 1

HCID 59293687HCID 59293687, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

Sodium hydroxide (pellets are finely grinded, 0.488 g, 12.2 mmol, 5 eq) is added to a solution of 4-[1-(4-bromo-pyridin-2-yl)-1-methyl-ethyl]-phenol (Step 55.2) (0.714 g, 2.44 mmol) in DMF (5 mL). The mixture is stirred for 20 min at rt. 3-Dimethylamino-1-propylchloride hydrochloride (0.611 g, 3.87 mmol, 1.6 eq) is added. The reaction mixture is heated to 90° C., stirred for 10 h, allowed to cool, diluted with EtOAc/H2O and extracted with EtOAc. The organic phase is washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) to afford 0.398 g of the title compound as an impure brown oil which is used without further purification: ESI-MS: 377.1/379.0 [M+H]+; TLC: Rf=0.22 (DCM/MeOH/NH3aq, 94:5:1).

Workup

  1. temperatureThe reaction mixture is heated to 90° C.
  2. stirringstirred for 10 h
  3. temperatureto cool
  4. extractionextracted with EtOAc
  5. washThe organic phase is washed with H2O and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Sources & evidence

ORD record
ord-0ddac76276574622a385d3c2be941feb
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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