2-(Isopropylamino)ethanol → 2-[N-Isopropyl-N-(2-benzoxazolyl)amino]ethanol

HRID 2119916Notes

Reaction equation

HRID 2119916 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:11]([NH:14][CH2:15][CH2:16][OH:17])([CH3:13])[CH3:12].C(N(CC)CC)C>O1CCCC1>[CH:11]([N:14]([CH2:15][CH2:16][OH:17])[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 79942-(Isopropylamino)ethanolHCID 8471TriethylamineHCID 119862-Chlorobenzoxazole

Product 1

HCID 101048742-[N-Isopropyl-N-(2-benzoxazolyl)amino]ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chlorobenzoxazole (23.04 g) was added dropwise to an ice-cooled solution of 2-(isopropylamino)ethanol (15.45 g) and triethylamine (30.3 g) in tetrahydrofuran (500 ml). The mixture was stirred at room temperature for 30 minutes, then heated at reflux overnight before being cooled and evaporated. The residue was dissolved in dichloromethane (800 ml) and washed with saturated sodium bicarbonate solution (500 ml), water (3×1 l) brine (1 l), dried (MgSO4), filtered and evaporated. The title compound was obtained as an oil following chromatography on silica gel using 1.5% methanol-dichloromethane as solvent.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperaturebefore being cooled
  4. customevaporated
  5. dissolutionThe residue was dissolved in dichloromethane (800 ml)
  6. washwashed with saturated sodium bicarbonate solution (500 ml), water (3×1 l) brine (1 l)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-415e1b5444bd47efbb08fa59b31bed57
Source dataset
uspto-grants-2004_02
Patent number
US06686475B2

Reaction notes

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