Isopropylamine → Isopropylpent-4-enylamine

HRID 1511587Notes

Reaction equation

HRID 1511587 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

3

Reactant 2

HCID 6363IsopropylamineHCID 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

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

Sources & evidence

ORD record
ord-10bb1bb12c72442182f0e9424001ecec
Source dataset
uspto-grants-2012_07
Patent number
US08216999B2

Reaction notes

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