Methylamine → N-Methyl-3-(phenylmethoxy)-1-propanamine

HRID 1837269Notes

Reaction equation

HRID 1837269 reaction equation
[CH3:1][NH2:2].Br[CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[CH2:8]([O:7][CH2:6][CH2:5][CH2:4][NH:2][CH3:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 2776064Benzyl 3-Bromopropyl Ether

Product 1

HCID 23497039N-Methyl-3-(phenylmethoxy)-1-propanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.57 g of methylamine is condensed in a solution of 1.8 ml of (3-bromo-propoxymethyl)-benzene 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. 1.91 g of (3-benzyloxy-propyl)-methyl-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-0fbd7af9fbb546fe9f252085efa052d8
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

Loading…