Ethanol → 2-(decylamino)ethanol

HRID 1278894Notes

Reaction equation

HRID 1278894 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-3567ad09047f4b87a323497420c9eef7
Source dataset
uspto-grants-2002_09
Patent number
US06444786B1

Reaction notes

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