Naproxen → HCID 131736273, compound

HRID 1052942Notes

Reaction equation

HRID 1052942 reaction equation
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:8]=[CH:7][C:6]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:5]=2[CH:4]=1.[CH3:18][N:19]([CH2:21][C@H:22]1[C@:27]([OH:36])([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH3:20]>CO>[CH3:20][N:19]([CH2:21][C@H:22]1[C@:27]([OH:36])([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH3:18].[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:8]=[CH:7][C:6]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 156391NaproxenHCID 667511(-)-(S,S)-trans-Tramadol

Product 1

HCID 131736273HCID 131736273, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of (S)-naproxen (2.14 g, 9.3 mmol) in 20 mL of methanol was added in 10 minutes to a stirred solution of (−)-tramadol (2.45 g, 9.3 mmol) in 10 mL of methanol. The resulting solution was stirred at room temperature for 30 minutes and the solvent was evaporated under vacuum rendering a light yellow oil. The oil was cooled to −197° C. and allowed to warm to room temperature to give the amorphous (−)-tramadol-(S)-naproxen salt as a white solid (4.59 g, 100%).

Workup

  1. customthe solvent was evaporated under vacuum
  2. temperatureThe oil was cooled to −197° C.
  3. temperatureto warm to room temperature

Sources & evidence

ORD record
ord-ec498e5756d34fc18c017273e81e1cc1
Source dataset
uspto-grants-2016_07
Patent number
US09393220B2

Reaction notes

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