Methylamine → N-Methyl-2-(4-methylphenyl)ethan-1-amine

HRID 1838920Notes

Reaction equation

HRID 1838920 reaction equation
[CH3:1][NH2:2].S(C1C=CC(C)=CC=1)(O[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=O)=O>O1CCCC1>[CH3:1][NH:2][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 2853862-(4-Methylphenyl)ethyl 4-methylbenzene-1-sulfonate

Product 1

HCID 22898654N-Methyl-2-(4-methylphenyl)ethan-1-amineYield 180.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.2 g of methylamine are condensed at −20° C. into a solution of 5.8 g of 2-p-tolylethyl tosylate in 15 ml of abs. tetrahydrofuran and the mixture is stirred overnight at room temperature in a pressure vessel. After the pressure vessel has been opened at −20° C., it is allowed to come to room temperature in order to allow excess methylamine to evaporate. The reaction solution is taken up in ether, washed with water and saturated sodium chloride solution, dried over magnesium sulphate and concentrated to dryness in vacuo. 5.39 g of methyl-(2-p-tolylethyl)amine are obtained, which is reacted further as a crude product.

Workup

  1. customhas been opened at −20° C.
  2. customto come to room temperature in order
  3. customto evaporate
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-b35780ae1b2b434e9cd9b2a11ab538f2
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

Loading…