Salicylic Acid → HCID 178455877, compound

HRID 875300Notes

Reaction equation

HRID 875300 reaction equation
[CH3:1][CH2:2][C@H:3]([C@H:11]([CH2:13][N:14]([CH3:16])[CH3:15])[CH3:12])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1.[C:17]([OH:26])(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20]>C(#N)C>[CH3:1][CH2:2][C@H:3]([C@H:11]([CH2:13][N:14]([CH3:16])[CH3:15])[CH3:12])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1.[C:17]([O-:26])(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20]

Participants

4

Reactant 2

HCID 338Salicylic AcidHCID 9838022Tapentadol

Product 1

HCID 178455877HCID 178455877, compoundYield 99.75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82.5 °C

Procedure

Tapentadol (2 g) was dissolved in acetonitrile (15 ml), followed by addition of salicylic acid (1.25 g) to the solution at 25-30° C. and heating the reaction mass at 80-85° C. The resulting solution was slowly cooled to 20-25° C. and stirred for 2 hours at 20-25° C. The resulting solid was collected by filtration, washed with acetonitrile (10 ml) and dried at 40-45° C. under vacuum to give 2.5 g of tapentadol salicylate salt (Purity by HPLC: 99.75%).

Workup

  1. temperatureThe resulting solution was slowly cooled to 20-25° C.
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with acetonitrile (10 ml)
  4. customdried at 40-45° C. under vacuum

Sources & evidence

ORD record
ord-72e258e0d24a486fba0be080945d769e
Source dataset
uspto-grants-2015_03
Patent number
US08981154B2

Reaction notes

Loading…