Ethanol → 2-(decylamino)ethanol

HRID 1282268Notes

Reaction equation

HRID 1282268 reaction equation
[NH2:1]C(O)C.Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH2:16]([OH:18])[CH3:17]>>[CH2:6]([NH:1][CH2:17][CH2:16][OH:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 702EthanolHCID 81731-BromodecaneHCID 522583Acetaldehyde ammonia

Product 1

HCID 40609082-(decylamino)ethanol

Procedure

A solution of aminoethanol (30.5 g, 500 mmol, 30.1 mL) and 1-bromodecane (27.65 g, 125 mmol, 26 mL) in ethanol was stirred at 65° C. for 4 hr. The solvent was removed under reduced pressure. The residue was diluted with EtOAc (800 mL) and the organic solution was washed with H2O (2×200 mL); saturated aqueous NaHCO3 (200 mL) and saturated brine (200 mL). The organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The resulting crude product, 2-(decylamino)ethanol, was used without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with EtOAc (800 mL)
  3. washthe organic solution was washed with H2O (2×200 mL)
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product, 2-(decylamino)ethanol, was used without further purification

Sources & evidence

ORD record
ord-4e9e7e7bf12a4aa9962579c5b14b83eb
Source dataset
uspto-grants-2002_09
Patent number
US06455669B1

Reaction notes

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