Diethyl Ether → (2-Ethyl-3-methoxybenzyl)dimethylamine

HRID 1178518Notes

Reaction equation

HRID 1178518 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]([CH3:9])[CH3:8].[CH2:13]([Li])[CH2:14]CC.ICC.C(OCC)C>C1COCC1>[CH2:13]([C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[CH:10][C:5]=1[CH2:6][N:7]([CH3:9])[CH3:8])[CH3:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6340IodoethaneHCID 5474343-Methoxy-N,N-dimethylbenzylamineHCID 178418339Butyllithium

Product 1

HCID 13780987(2-Ethyl-3-methoxybenzyl)dimethylamineYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(3-Methoxybenzyl)dimethylamine (2.03 mL, 2.00 g, 12.1 mmol) was dissolved in anhydrous THF (20 mL) under nitrogen and cooled to 0° C. with an ice-water bath. Butyllithium (2.5M in hexanes, 5.3 mL, 13.3 mmol) was added dropwise via syringe over 10 min (temperature kept below 5° C.). After stirring at 0° C. for 2 h, iodoethane (1.1 mL, 2.1 g, 13.8 mmol) was added dropwise via syringe over 25 min (temperature kept below 5° C.). The reaction mixture was allowed to reach ambient temperature. After 4 h, the reaction contents were transferred with diethyl ether and adsorbed onto silica gel (3.8 g) upon removal of the solvent in vacuo. Chromatography gave (2-ethyl-3-methoxybenzyl)dimethylamine (1.30 g, 56%) as a pale yellow solid.

Workup

  1. customto reach ambient temperature
  2. waitAfter 4 h
  3. customthe reaction contents
  4. customadsorbed onto silica gel (3.8 g) upon removal of the solvent in vacuo

Sources & evidence

ORD record
ord-f4a7ca5226784c648e15b1a1be21108e
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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