2-Methoxyethylamine → N-(2-methoxyethyl)aniline

HRID 341502Notes

Reaction equation

HRID 341502 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][O:11][CH2:12][CH2:13][NH2:14]>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:10][O:11][CH2:12][CH2:13][NH:14][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 80182-MethoxyethylamineHCID 66827Phenylboronic Acid

Product 1

HCID 1581105N-(2-methoxyethyl)anilineYield 17.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To phenylboronic acid (5 g, 41.0 mmol) in DCM (50 mL) was added copper (II) acetate (0.78 g, 4.1 mmol) and the mixture was stirred for 5 min at room temperature. 2-Methoxyethanamine (3.08 g, 41.0 mmol) was added and the mixture was stirred at 40 C for 19 h. The mixture was then passed through a silica plug and then purified by FCC, eluting with 10% EtOAc in heptane to afford the title compound (1.065 g, 17% yield). Method B HPLC-MS: MH+ requires m/z=152 Found: m/z=152, Rt=1.08 min (87%).

Workup

  1. stirringthe mixture was stirred at 40 C for 19 h
  2. custompurified by FCC
  3. washeluting with 10% EtOAc in heptane

Sources & evidence

ORD record
ord-a468ee374f834676a1a6eea7fdd2a8a2
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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