Ethanolamine → 2-(4-Pyridine-2-ylbenzoylamino)ethanol

HRID 1860108Notes

Reaction equation

HRID 1860108 reaction equation
C(N(CC)CC)C.Cl.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.[CH2:24]([CH2:26][NH2:27])[OH:25]>ClCCl>[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:27][CH2:26][CH2:24][OH:25])=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 186259104-(2-Pyridinyl)benzoyl Chloride Hydrochloride

Product 1

HCID 186260452-(4-Pyridine-2-ylbenzoylamino)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.14 ml) was added to a suspension of 4-pyridine-2-ylbenzoylchloride hydrochloride (254 mg) in dichloromethane (2 ml). To the mixture a solution of ethanolamine (0.060 ml) in dichloromethane (3 ml) was added. This mixture was stirred for 30 minutes. At the end of this time the reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with aqueous sodium chloride and dried over anhydrous magnesium sulfate and concentrated to afford crystals. The crystals were washed with isopropyl ether to afford the title compound (111 mg).

Workup

  1. concentrationAt the end of this time the reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed with aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto afford crystals
  8. washThe crystals were washed with isopropyl ether

Sources & evidence

ORD record
ord-c153b5dbf4ee48728e46e47f9136b404
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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