Methylamine → 2-(2-methoxyphenoxy)-N-methylethanamine

HRID 2297569Notes

Reaction equation

HRID 2297569 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12].[CH3:13][NH2:14]>C(O)C>[CH3:12][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][NH:14][CH3:13]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 17990992-(2-Bromoethoxy)anisole

Product 1

HCID 64854412-(2-methoxyphenoxy)-N-methylethanamineYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(2-bromoethoxy)-2-methoxybenzene (7d) (7.7 g, 33 mmol) in a 33% solution of methylamine in ethanol was heated at 80° C. in a sealed tube for 16 h. After cooling to room temperature, the solvents were evaporated in vacuo. A 2N aqueous solution of sodium hydroxide was added to the remaining oil and the resulting slurry was extracted with ethyl acetate (2×250 mL). The collected organic phases were dried (Na2SO4) and the solvents evaporated in vacuo giving 5.9 g (98%) of the title compound as an oil: 1H NMR (CDCl3) δ 1.85 (broad s, 1H), 2.50 (s, 3H), 3.00 (t, 2H), 3.85 (s, 3H), 4.10 (t, 2H), 6.85-6.95 (m, 4H).

Workup

  1. customthe solvents were evaporated in vacuo
  2. additionA 2N aqueous solution of sodium hydroxide was added to the remaining oil
  3. extractionthe resulting slurry was extracted with ethyl acetate (2×250 mL)
  4. dry with materialThe collected organic phases were dried (Na2SO4)
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-4c46427fac9a43dbbac67362b16ecd82
Source dataset
uspto-grants-2002_12
Patent number
US06492374B2

Reaction notes

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