Benzyl Alcohol → Bis(dimethylaminoethyl) ether

HRID 1670854Notes

Reaction equation

HRID 1670854 reaction equation
[CH2:1]([OH:8])[C:2]1C=CC=CC=1.[H-].[Na+].Cl.Cl[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16].[Li+].[Cl-].[CH3:20][N:21](C=O)[CH3:22]>C(OCC)(=O)C>[CH3:16][N:15]([CH2:14][CH2:13][O:8][CH2:1][CH2:2][N:21]([CH3:22])[CH3:20])[CH3:17]

Participants

7

Reactant 5

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 433294Lithium ChlorideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 18204Bis(dimethylaminoethyl) ether

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask, 300 mg (0.923 mmol) of 2 was dissolved in 12 mL of DMF. To this solution, 92 mg (2.30) of NaH (60% dispersion in mineral oil) was added and stirred for 10 minutes followed by addition of 146 mg (1.01 mmol) of (2-chloro-ethyl)-dimethyl-amine hydrogen chloride. This reaction mixture was stirred at 70° C. for 12 hours and allowed to cool to room temperature. Ethyl acetate and 10% LiCl were added. The organic layer was washed with this LiCl solution three times, distilled water and brine. The organic layer was dried with Na2SO4, filtered and concentrated to afford 380 mg of crude product 3, which was taken on without further purification.

Workup

  1. stirringThis reaction mixture was stirred at 70° C. for 12 hours
  2. washThe organic layer was washed with this LiCl solution three times
  3. distillationdistilled water and brine
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-057999ee49674317a9049a822c0705de
Source dataset
uspto-grants-2011_08
Patent number
US07994172B2

Reaction notes

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