Ethanolamine → HCID 22051221, compound

HRID 1831003Notes

Reaction equation

HRID 1831003 reaction equation
[H-].[Na+].[CH2:3]([CH2:5][NH2:6])[OH:4].Cl[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1>O1CCCC1>[NH3:6].[C:9]1([CH2:8][O:4][CH2:3][CH2:5][NH2:6])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 68451-ChloromethylnaphthaleneHCID 24758Sodium hydride

Product 2

HCID 222AmmoniaHCID 22051221HCID 22051221, compoundYield 71,547.703%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.00 g, 0.025 mmol) was added portionwise to a cooled (0° C.) solution of ethanolamine (1.51 ml, 0.025 mmol) in tetrahydrofuran (25 ml). The reaction mixture was then heated to reflux for 30 minutes. Chloromethylnaphthalene (3.4 ml, 0.0225 mmol) was added and the reaction mixture heated at reflux for a further 3 hours. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. The residue was partitioned between dichloromethane (50 ml) and 1 N aqueous sodium hydroxide (50 ml). The organic phase was separated and the aqueous phase extracted with dichloromethane (2×50 ml). The combined organic extracts were reduced in vacuo and the residue purified by flash column chromatography eluting with dichloromethane:methanol: 880 ammonia (98:2:0.2 changing to 90:10:1 by volume) to give the title compound as a colourless oil (1.80 g, 40%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethe reaction mixture heated
  4. temperatureat reflux for a further 3 hours
  5. customthe solvent removed in vacuo
  6. customThe residue was partitioned between dichloromethane (50 ml) and 1 N aqueous sodium hydroxide (50 ml)
  7. customThe organic phase was separated
  8. extractionthe aqueous phase extracted with dichloromethane (2×50 ml)
  9. customthe residue purified by flash column chromatography
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-c84372debee843a49594e820a9781f3d
Source dataset
uspto-grants-2006_06
Patent number
US07067541B2

Reaction notes

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