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

HRID 1633697Notes

Reaction equation

HRID 1633697 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

In anaolgy to Geri, Roberto; Polizzi, Carmela; Lardicci, Luciano; Caporusso, Anna Maria; Gazz.Chim.Ital.; 124; 6; 1994; 241-248: 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. 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 (pH9), it
  5. extractionwas extracted with ether
  6. dry with materialThe ether phase was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fed81469bd97404f8cb17b37c97038cf
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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