(3-Methoxy-2-propylbenzyl)-dimethylamine → 3-Dimethylaminomethyl-2-propylphenol hydrobromide

HRID 1243741Notes

Reaction equation

HRID 1243741 reaction equation
C[O:2][C:3]1[C:4]([CH2:13][CH2:14][CH3:15])=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]([CH3:9])[CH3:8].[BrH:16].C(O)(=O)C>>[BrH:16].[CH3:9][N:7]([CH2:6][C:5]1[C:4]([CH2:13][CH2:14][CH3:15])=[C:3]([OH:2])[CH:12]=[CH:11][CH:10]=1)[CH3:8]

Participants

3

Reactant 2

HCID 13780988(3-Methoxy-2-propylbenzyl)-dimethylamineHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 137809963-Dimethylaminomethyl-2-propylphenol hydrobromideYield 79%

Procedure

(3-Methoxy-2-propylbenzyl)-dimethylamine (1.51 g, 7.28 mmol) was suspended in 30% hydrogen bromide/acetic acid (10 mL) and heated to reflux with stirring for 20 h. The cooled reaction mixture was triturated and decanted with successive portions of diethyl ether (4×), then triturated with diethyl ether overnight. The solid was collected by filtration, washed with ether and dried to give 3-dimethylaminomethyl-2-propylphenol hydrobromide (1.58 g, 79%) 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 (4×)
  6. customtriturated with diethyl ether overnight
  7. filtrationThe solid was collected by filtration
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-0d750c46383e46e4bc504d0d5f7b111f
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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