Ethanolamine → (RS)-1-(6-chloropyridin-3-yl)-2-(2-hydroxyethylamino)ethanol

HRID 2403290Notes

Reaction equation

HRID 2403290 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][O:9]2)=[CH:4][N:3]=1.[NH2:11][CH2:12][CH2:13][OH:14].CCOC(C)=O.C1COCC1>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]([OH:9])[CH2:10][NH:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 21939870Tetrahydrofuran ethyl acetateHCID 221713512-Chloro-5-(oxiran-2-yl)pyridine

Product 1

HCID 86671393(RS)-1-(6-chloropyridin-3-yl)-2-(2-hydroxyethylamino)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (RS)-2-chloro-5-(oxiran-2-yl)pyridine (4.0 g) in THF (15 ml) was added 2-aminoethanol (15.4 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into EtOAc/THF (1:1) and the mixture was washed with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford (RS)-1-(6-chloropyridin-3-yl)-2-(2-hydroxyethylamino)ethanol (5.05 g) as a yellow solid which was used in the next step without further purification. MS (ISP): 219.3 ([{37Cl}M+H]+), 217.2 ([{35Cl}M+H]+), 201.3 ([{37Cl}M+H—H2O]+), 199.1 ([{35Cl}M+H—H2O]+).

Workup

  1. washthe mixture was washed with saturated brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e07517f2b8cb4bc2b9d823257bac8405
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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