Ethanolamine → 2-[(2-Hydroxyethyl)amino]-N-3-pyridinylacetamide

HRID 2213045Notes

Reaction equation

HRID 2213045 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1.C(N(CC)CC)C.[NH2:20][CH2:21][CH2:22][OH:23]>O1CCCC1.CO>[OH:4][CH2:3][CH2:2][NH:20][CH2:21][C:22]([NH:12][C:8]1[CH:7]=[N:6][CH:11]=[CH:10][CH:9]=1)=[O:23]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 100093-Aminopyridine

Product 1

HCID 218650052-[(2-Hydroxyethyl)amino]-N-3-pyridinylacetamideYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Chloroacetyl chloride (2.2 mL, 27.6 mmol) was added dropwise over 10 minutes to a stirred, cooled (0° C.) solution of 3-pyridinamine (2 g, 21 mmol) and triethylamine (4 mL, 28 mmol) in tetrahydrofuran (30 mL). The mixture was allowed to warm to room temperature, then 2-aminoethanol (5 mL, 120 mmol) in methanol (5 mL) was added. The mixture was stirred at 60° C. for 4 hours, cooled and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH/NH3(Aq.) (90:10:1), to give the title compound (2.53 g, 62%). m/z (ES+) 196 (M+1).

Workup

  1. temperaturecooled
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by flash column chromatography on silica gel
  4. washeluting with CH2Cl2/MeOH/NH3(Aq.) (90:10:1)

Sources & evidence

ORD record
ord-97c5dfdf6faf48d2be69ea37f8365166
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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