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Ethanolamine → HCID 22951276, compound

HRID 276255
Notes
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Reaction equation

HRID 276255 reaction equation
Br[CH2:2][C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1.[NH2:9][CH2:10][CH2:11][OH:12]>ClC=C(Cl)Cl.[OH-].[Na+]>[OH:12][CH2:11][CH2:10][NH:9][CH2:2][C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 700EthanolamineHCID 30159321-(Bromomethyl)cyclohexene

Product 1

HCID 22951276HCID 22951276, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6575TrichloroethyleneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-bromomethyl-1-cyclohexene (3.25 g) and 2-aminoethanol (6 mL) in trichloroethylene (40 mL) was heated at the reflux temp. for 3 d, cooled to room temp., and diluted with a 1N NaOH solution (30 mL). The aqueous layer was extracted with CH2Cl2 (4×20 mL) and the combined organic layers were washed with H2O (30 mL) and a saturated NaCl solution (30 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by vacuum distillation to give N-hydroxyethyl-N-cyclohex-1-enylmethylamine as a colorless oil (1.78 g, 62%): bp 92-94° C. (6 mmHg),

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. temperaturecooled to room temp.
  2. extractionThe aqueous layer was extracted with CH2Cl2 (4×20 mL)
  3. washthe combined organic layers were washed with H2O (30 mL)
  4. dry with materiala saturated NaCl solution (30 mL), dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. distillationThe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-b364ae2a91544f22b589f234249abcce
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06353006B1

Reaction notes

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