Naproxen → HCID 131736273, compound

HRID 1052943Notes

Reaction equation

HRID 1052943 reaction equation
[CH3:1][N:2]([CH2:4][C@H:5]1[C@:10]([OH:19])([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:3].[CH3:20][C@H:21]([C:34]([OH:36])=[O:35])[C:22]1[CH:27]=[CH:26][C:25]2[CH:28]=[C:29]([O:32][CH3:33])[CH:30]=[CH:31][C:24]=2[CH:23]=1>C(O)(C)C>[CH3:3][N:2]([CH2:4][C@H:5]1[C@:10]([OH:19])([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:1].[CH3:20][C@H:21]([C:34]([OH:36])=[O:35])[C:22]1[CH:27]=[CH:26][C:25]2[CH:28]=[C:29]([O:32][CH3:33])[CH:30]=[CH:31][C:24]=2[CH:23]=1

Participants

4

Reactant 2

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

Product 1

HCID 131736273HCID 131736273, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of (−)-tramadol (0.58 g, 2.20 mmol) in 2 mL of isopropanol was added to a stirred suspension of (S)-naproxen (1.02 g, 4.43 mmol, 2 eq) in 2 mL of isopropanol at 60° C. The resulting solution was cooled to room temperature and a third of the solvent was evaporated. The solution was seeded with 5-10 mg of crystalline (−)-tramadol-(S)-naproxen (1:2) co-crystal and was left standing at room temperature for 48 hours without stirring. The resulting suspension was filtered off, the filtrate was washed with ca. 1 mL of isopropanol and dried under vacuum (10 mm Hg) at 60° C. for 24 hours to give the co-crystal (−)-tramadol-(S)-naproxen in a 1:2 ratio as a white solid (1.31 g, 81%).

Workup

  1. customa third of the solvent was evaporated
  2. waitwas left
  3. filtrationThe resulting suspension was filtered off
  4. washthe filtrate was washed with ca. 1 mL of isopropanol
  5. customdried under vacuum (10 mm Hg) at 60° C. for 24 hours

Sources & evidence

ORD record
ord-4b218c9f90154e579b2aebf14743788b
Source dataset
uspto-grants-2016_07
Patent number
US09393220B2

Reaction notes

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