Methylamine → Methyl(3-phenoxypropyl)amine

HRID 1837268

Reaction equation

HRID 1837268 reaction equation
[CH3:1][NH2:2].[O:3]([CH2:10][CH2:11][CH2:12]Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[CH3:1][NH:2][CH2:12][CH2:11][CH2:10][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 68522Benzene, (3-bromopropoxy)-

Product 1

HCID 22067856Methyl(3-phenoxypropyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.57 g of methylamine is condensed in a solution of 1.6 ml of 3-phenoxy-propylbromide in 15 ml of anhydrous tetrahydrofuran at −78° C., and it is stirred overnight at room temperature in a pressurized reactor. After the pressurized reactor was opened at −20° C., it is allowed to come to room temperature to allow excess methylamine to evaporate off. Then, the reaction solution is added to saturated sodium chloride solution, extracted with ether, dried on magnesium sulfate and concentrated by evaporation in a vacuum. 2.01 g of methyl-(3-phenoxy-propyl)-amine is obtained as a crude product, which is used without further purification in the next stage.

Workup

  1. customwas opened at −20° C.
  2. customto come to room temperature
  3. customto evaporate off
  4. additionThen, the reaction solution is added to saturated sodium chloride solution
  5. extractionextracted with ether
  6. customdried on magnesium sulfate
  7. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-fc7b3c344a2b4cff8abb4059c487e8b0
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Linked notes

Loading…