Water → Cyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, hydrochloride (1:1)
Reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:3].C([O-])(=O)C1C(=CC=CC=1)O.O.[OH-].[K+].C(Cl)[Cl:34]>>[CH3:3][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:1].[ClH:34]Participants
Conditions
- Temperature
- 15 °C
Procedure
In a reaction flask 29 g tramadol salicylate salt was stirred with 87 ml water and pH was adjusted to 11-12 by 10% aqueous KOH solution. The tramadol free base was extracted with methylene chloride, organic extract washed with water, and methylene chloride was evaporated under reduced pressure. The oil obtained was dissolved in 88.0 ml methylene chloride. Stirred and cooled to 15° C. Adjusted pH to 2-2.5 by conc. HCI. Stirred for 1.0 hour at same temperature. Raised the temperature to 25-30° C. and stirred it for 30 minutes. Distilled out solvent completely under vacuum. Charged 42 ml acetone and stirred at 25-30° C. for 30 minutes. Filtered the product and washed solid with acetone. Yield=18.4 gm (85%) (cis=99.98% & trans=0.02% by HPLC area%).
Workup
- extractionThe tramadol free base was extracted with methylene chloride
- extractionorganic extract
- washwashed with water, and methylene chloride
- customwas evaporated under reduced pressure
- customThe oil obtained
- stirringStirred for 1.0 hour at same temperature
- temperatureRaised the temperature to 25-30° C.
- stirringstirred it for 30 minutes
- distillationDistilled out solvent completely under vacuum
- additionCharged 42 ml acetone
- stirringstirred at 25-30° C. for 30 minutes
- filtrationFiltered the product
- washwashed solid with acetone
Sources & evidence
- ORD record
- ord-9d8496f38e66440ba33cad5a6da4f742
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470816B2
Reaction notes
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