Isopropylamine → Isopropylpent-4-enylamine

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[CH:7]([NH2:10])([CH3:9])[CH3:8]>>[CH:7]([NH:10][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6])([CH3:9])[CH3:8]

Participants

Reactant 2

HCID 6363Isopropylamine

HCID 707041-Pentene, 5-bromo-

Product 1

HCID 551578Isopropylpent-4-enylamineYield 40%

Conditions

Temperature: 60 °C

Procedure

5-Bromo-1-pentene (42.3 mmol) was added to isopropylamine (423 mmol), and the mixture was stirred at 60° C. for 48 h in the dark in a sealed tube. Then the volatiles were evaporated at reduced pressure and the crude residue was dissolved in 50 mL of diethyl ether and washed twice with water. The organic phase was dried over Na2SO4. Evaporation of the solvent gave N-isopropylpent-4-en-1-amine as brownish oil (40%) which was used without any further purification.

Workup

customThen the volatiles were evaporated at reduced pressure
dissolutionthe crude residue was dissolved in 50 mL of diethyl ether
washwashed twice with water
dry with materialThe organic phase was dried over Na2SO4
customEvaporation of the solvent

Sources & evidence

ORD record: ord-10bb1bb12c72442182f0e9424001ecec
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08216999B2

Reaction notes

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