3-(Diethylamino)phenol → 3-[(3-bromopropyl)oxy]-N,N-diethylaniline

HRID 533857

Reaction equation

HRID 533857 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:2].[Br:13][CH2:14][CH2:15][CH2:16]Br.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[Br:13][CH2:14][CH2:15][CH2:16][O:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[N:3]([CH2:1][CH3:2])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 70623-(Diethylamino)phenolHCID 80011,3-DibromopropaneHCID 10796Cesium carbonate

Product 1

HCID 689633743-[(3-bromopropyl)oxy]-N,N-diethylanilineYield 17.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(diethylamino)phenol (0.0104 g, 0.631 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.640 mL, 6.30 mmol) followed by Cs2CO3 (0.313 g, 0.961 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DCM (8 mL). The organic layer was dried through a phase separator and concentrated under vacuum. The residue was taken up in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.0314 g, 17.4%). EI-MS m/z 286(M+H+) Rt (1.59 min).

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe resulting residue was treated with H2O (4 mL)
  3. extractionextracted with DCM (8 mL)
  4. customThe organic layer was dried through a phase separator
  5. concentrationconcentrated under vacuum
  6. custompurified by preparatory HPLC (without TFA)

Sources & evidence

ORD record
ord-71a2f545bc2a4cffa87f06e709b94c98
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Linked notes

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