Ethylamine → N-ethyl-6,6-dimethyl-2,4-heptadiynylamine hydrochloride

HRID 1464768Notes

Reaction equation

HRID 1464768 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH2:5]([NH2:7])[CH3:6].[ClH:8].NO.Br[C:12]#[C:13][C:14]([CH3:17])([CH3:16])[CH3:15].C(C#C)(C)(C)C.BrBr>[Cu]Cl.CO>[ClH:8].[CH2:5]([NH:7][CH2:1][C:2]#[C:3][C:12]#[C:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:6]

Participants

9

Reactant 6

HCID 6341EthylamineHCID 7842Propargyl bromideHCID 135123,3-Dimethyl-1-butyneHCID 24408BromineHCID 443297Hydroxyamine hydrochlorideHCID 103295731-Butyne, 1-bromo-3,3-dimethyl-

Product 1

HCID 19917158N-ethyl-6,6-dimethyl-2,4-heptadiynylamine hydrochloride

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolvent2×

Procedure

A methanol solution (7.5 ml) of 0.75 ml of propargyl bromide was added dropwise to 6 ml of a 70% aqueous solution of ethylamine with stirring and ice cooling, and the mixture was stirred for 1.5 hours. 120 mg of copper(I) chloride and 100 mg of hydroxylamine hydrochloride were added, and to this solution, a methanol solution(3 ml) of 5.6 mg of 1-bromo-3,3-dimethyl-1-butyne [synthesized by a bromination of lithiated tert-butylacetylene with bromine ] was added dropwise under ice cooling. The mixture was stirred at room temperature for 2 hours, and then the solvent was evaporated. The residue was worked up in a customary manner, and the product was treated with a methanol solution of hydrogen chloride to give 0.94 g of the captioned hydrochloride as a white crystalline powder.

Workup

  1. stirringice cooling, and the mixture was stirred for 1.5 hours
  2. additionwas added dropwise under ice cooling
  3. stirringThe mixture was stirred at room temperature for 2 hours
  4. customthe solvent was evaporated
  5. additionthe product was treated with a methanol solution of hydrogen chloride

Sources & evidence

ORD record
ord-93a22b9832d44db8a3ae8492142dfd8f
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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