Ethylamine → (E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride

HRID 1648608Notes

Reaction equation

HRID 1648608 reaction equation
[CH2:1]([NH2:3])[CH3:2].[Cl:4][CH:5]=[CH:6][CH2:7]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:28]([C:32]#[CH:33])([CH3:31])([CH3:30])[CH3:29]>[Cu]I.[Pd](Cl)Cl>[ClH:4].[CH3:29][C:28]([CH3:31])([CH3:30])[C:32]#[C:33]/[CH:5]=[CH:6]/[CH2:7][NH:3][CH2:1][CH3:2]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 11776TriphenylphosphineHCID 135123,3-Dimethyl-1-butyneHCID 248831,3-Dichloropropene

Product 1

HCID 19917114(E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochlorideYield 74%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

By using 145 ml (1.79 mol) of 70% ethylamine aqueous solution instead of n-propylamine, 255 ml of tetahydrofuran, 27.3 ml (0.296 mol) of 1,3-dichloropropene (E/Z =9/1), 2.85 g (15 mmol) of copper (I) iodide, 1.07 g (6.0 mmol) of palladium chloride, 3.15 g (12 mmol) of triphenylphosphine and 45.0 ml (0.365 mol) of tert-butylacetyiene, the treatment was conducted in the same manner as in Example 1 to obtain 44.4 g (yield: 74%) of the above identified compound as slightly yellowish brown crystalline powder.

Workup

  1. customto obtain 44.4 g (yield: 74%) of the

Sources & evidence

ORD record
ord-36981e53d3024be78f8be6177b007a23
Source dataset
uspto-grants-1995_07
Patent number
US05436354

Reaction notes

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