Hydrogen Bromide → 1-(N,N-dimethylamino)methyl-3-hydroxy-2-propylbenzene

HRID 1289150Notes

Reaction equation

HRID 1289150 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]C)[C:6]=1[CH2:13][CH2:14][CH3:15])[CH3:3].Br>C(O)(=O)C>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=1[CH2:13][CH2:14][CH3:15])[CH3:1]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 13780988(3-Methoxy-2-propylbenzyl)-dimethylamine2×

Product 1

HCID 137809951-(N,N-dimethylamino)methyl-3-hydroxy-2-propylbenzeneYield 78.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The 1-(N,N-dimethylamino)methyl-3-methoxy-2-propylbenzene was then converted to the 3-hydroxy equivalent by adding the 1-(N,N-dimethylamino)methyl-3-methoxy-2-propylbenzene (238 g, 1.15 moles) to acetic acid (2.35 L) and then adding hydrobromic acid (1 L of a 48% solution). This mixture was then stirred at reflux for thirty hours. The acetic acid was removed and the residue was redissolved in ethanol. The ethanol was then removed and the residue was again redissolved in ethanol. Diethyl ether was added under a precipitate formed. Precipition was allowed to proceed overnight and the precipitate was collected by filtration to yield 216.2 grams (78.9%) of 1-(N,N-dimethylamino)methyl-3-hydroxy-2-propylbenzene hydrobromic salt.

Workup

  1. temperatureat reflux for thirty hours
  2. customThe acetic acid was removed
  3. dissolutionthe residue was redissolved in ethanol
  4. customThe ethanol was then removed
  5. dissolutionthe residue was again redissolved in ethanol
  6. additionDiethyl ether was added under a precipitate
  7. customformed
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ae1809cf09404d4fbd715bcf4dffd244
Source dataset
uspto-grants-1998_05
Patent number
US05747517

Reaction notes

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