Methylamine → (E)-N-methyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride

HRID 487772

Reaction equation

HRID 487772 reaction equation
[CH3:1][NH2:2].[Cl:3][CH:4]=[CH:5][CH2:6]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:27]([C:31]#[CH:32])([CH3:30])([CH3:29])[CH3:28]>[Cu]I.[Pd](Cl)Cl.O1CCCC1>[ClH:3].[CH3:28][C:27]([CH3:30])([CH3:29])[C:31]#[C:32]/[CH:4]=[CH:5]/[CH2:6][NH:2][CH3:1]

Participants

8

Reactant 4

HCID 6329MethylamineHCID 11776TriphenylphosphineHCID 135123,3-Dimethyl-1-butyneHCID 248831,3-Dichloropropene

Product 1

HCID 19917487(E)-N-methyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochlorideYield 70%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

By using 104 ml (3.02 mol) of 40% methylamine aqueous solution instead of n-propylamine, 85 ml of tetrahydrofuran, 9.10 ml (98.8 mmol) of 1,3-dichloropropene (E/Z =9/1), 950 mg (5 mmol) of copper (I) iodide, 355 mg (2 mmol) of palladium chloride, 1.05 g (4 mmol) of triphenylphosphine and 15.0 ml (0.121 mol) of tert-butylacetylene, the treatment was conducted in the same manner as in Example 1 to obtain 12.9 g (yield: 70%) of the above identified compound as off-white crystalline powder.

Workup

  1. customto obtain 12.9 g (yield: 70%) of the

Sources & evidence

ORD record
ord-be081e966b924843907e67a4b92e6cb2
Source dataset
uspto-grants-1994_03
Patent number
US05296612

Linked notes

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