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

HRID 966339Notes

Reaction equation

HRID 966339 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 (pH 9), it was extracted with ether. The ether phase was dried over Na2SO4 and concentrated. Destillation 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 (pH 9), it
  5. extractionwas extracted with ether
  6. dry with materialThe ether phase was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6c7fde7d2d7b4a268c2d4bfdef2c28c8
Source dataset
uspto-grants-2005_10
Patent number
US06951879B2

Reaction notes

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