3-(Dimethylamino)propyl chloride hydrochloride → HCID 59293687, compound

HRID 1516230Notes

Reaction equation

HRID 1516230 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)([CH3:11])[CH3:10])[CH:4]=1.Cl.[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24]Cl>CN(C=O)C.CCOC(C)=O.O>[Br:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:24][CH2:23][CH2:22][N:21]([CH3:26])[CH3:20])=[CH:16][CH:17]=2)([CH3:10])[CH3:11])[CH:4]=1

Participants

6

Reactant 3

HCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 5360545SodiumHCID 57417096HCID 57417096, compound

Product 1

HCID 59293687HCID 59293687, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

Sodium hydroxyde (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 31.2) (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-b8b77062ce104d21b9b0166eafbfc563
Source dataset
uspto-grants-2012_07
Patent number
US08227462B2

Reaction notes

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