(2-Ethyl-3-methoxybenzyl)dimethylamine → 3-Dimethylaminomethyl-2-ethylphenol hydrobromide

HRID 1243737Notes

Reaction equation

HRID 1243737 reaction equation
[CH2:1]([C:3]1[C:12]([O:13]C)=[CH:11][CH:10]=[CH:9][C:4]=1[CH2:5][N:6]([CH3:8])[CH3:7])[CH3:2].[BrH:15].C(O)(=O)C>>[BrH:15].[CH3:8][N:6]([CH2:5][C:4]1[C:3]([CH2:1][CH3:2])=[C:12]([OH:13])[CH:11]=[CH:10][CH:9]=1)[CH3:7]

Participants

3

Reactant 2

HCID 13780987(2-Ethyl-3-methoxybenzyl)dimethylamineHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 137809943-Dimethylaminomethyl-2-ethylphenol hydrobromideYield 78%

Procedure

(2-Ethyl-3-methoxybenzyl)dimethylamine (1.30 g, 6.73 mmol) was suspended in 30% hydrogen bromide/acetic acid (10 mL) and heated to reflux with stirring for 21 h. The cooled reaction mixture was triturated and decanted with successive portions of diethyl ether (3×), then triturated with diethyl ether overnight. The solid was collected by filtration, washed with ether and dried to give 3-dimethylaminomethyl-2-ethylphenol hydrobromide (1.37 g, 78%) as a tan solid.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customThe cooled reaction mixture
  4. customwas triturated
  5. customdecanted with successive portions of diethyl ether (3×)
  6. customtriturated with diethyl ether overnight
  7. filtrationThe solid was collected by filtration
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-0f0435553b6649439409c1152af78b86
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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