3-Methoxypropylamine → N-(3-Methoxypropyl)pentan-1-amine

HRID 622104Notes

Reaction equation

HRID 622104 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].[CH2:7](Br)[CH2:8][CH2:9][CH2:10][CH3:11]>C(O)(C)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 16723-MethoxypropylamineHCID 80571-Bromopentane

Product 1

HCID 14806244N-(3-Methoxypropyl)pentan-1-amineYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

891 g (10 moles) of 3-methoxypropylamine are mixed with one liter of isopropanol at ambient temperature in a reactor. 755 g (5 moles) of n-pentyl bromide are added to the solution and then heated under reflux (about 90° C.) for 12 hours. The solvent is evaporated at a reduced pressure, the residue diluted with two liters of 2N sodium carbonate, a supernatent oil is separated and distilled at reduced pressure, the 104°-8° C./20 mmHg fraction being collected. Thus 390 g of product are obtained. Yield 73%.

Workup

  1. temperatureheated
  2. customThe solvent is evaporated at a reduced pressure
  3. additionthe residue diluted with two liters of 2N sodium carbonate
  4. customa supernatent oil is separated
  5. distillationdistilled at reduced pressure
  6. customthe 104°-8° C./20 mmHg fraction being collected

Sources & evidence

ORD record
ord-131b59a607f34778b231e510bbdf9cb7
Source dataset
uspto-grants-1988_09
Patent number
US04769389

Reaction notes

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