2-(Ethylamino)ethanol → 2-[(1,1-Dimethyl-prop-2-ynyl)-ethyl-amino]-ethanol

HRID 270438Notes

Reaction equation

HRID 270438 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][OH:6])[CH3:2].Cl[C:8]([CH3:12])([CH3:11])[C:9]#[CH:10]>C1COCC1.Cl[Cu]>[CH3:11][C:8]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][OH:6])([CH3:12])[C:9]#[CH:10]

Participants

5

Reactant 2

HCID 80722-(Ethylamino)ethanolHCID 706791-Butyne, 3-chloro-3-methyl-

Product 1

HCID 223139772-[(1,1-Dimethyl-prop-2-ynyl)-ethyl-amino]-ethanol

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 14.3 ml (146.3 mmol) 2-Ethylaminoethanol in 60 ml THF were added 362 mg (3.7 mmol) CuCl, followed by 7.5 g (73.1 mmol) 3-Chloro-3-methyl-1-butyne. The solution was stirred at RT for 2 h, the solvent was removed and the residue dissolved in ether/2M HCl. The phases were separated and after addition of Na2CO3 to the aqueous phase (pH9), it was extracted with ether. The ether phase was dried over Na2SO4 and concentrated. Distillation by Kugelrohr yielded 2-[(1,1-Dimethyl-prop-2-ynyl)-ethyl-amino]-ethanol as colorless oil, MS: 155 (M).

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved in ether/2M HCl
  3. customThe phases were separated
  4. additionafter addition of Na2CO3 to the aqueous phase (pH9), it
  5. extractionwas extracted with ether
  6. dry with materialThe ether phase was dried over Na2SO4
  7. concentrationconcentrated
  8. distillationDistillation by Kugelrohr

Sources & evidence

ORD record
ord-678480f2f7c14030bd827a80e0438724
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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