Hydrochloric Acid → Tapentadol Hydrochloride

HRID 1771017Notes

Reaction equation

HRID 1771017 reaction equation
[ClH:1].[CH2:2]([C@@H:4]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17]CC2C=CC=CC=2)[CH:12]=1)[C@@H:5]([CH3:10])[CH2:6][N:7]([CH3:9])[CH3:8])[CH3:3]>O>[ClH:1].[CH3:9][N:7]([CH3:8])[CH2:6][C@H:5]([CH3:10])[C@H:4]([C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60164845(betaR,gammaR)-gamma-ethyl-N,N,beta-trimethyl-3-(phenylmethoxy)benzenepropanamine

Product 1

HCID 9838021Tapentadol HydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 mL of water and 20 mL of concentrated hydrochloric acid were added to the product of Example 38 (2.5 g, 8 mmol), then it was reacted at 80° C. for 17 hours, after that, the reaction solution was concentrated and recrystallized with isopropanol and isopropyl ether to give the target 1.9 g, yield: 90%. The HNMR spectrum data is the same as that in Example 7.

Workup

  1. customit was reacted at 80° C. for 17 hours
  2. concentrationafter that, the reaction solution was concentrated
  3. customrecrystallized with isopropanol and isopropyl ether
  4. customto give the target 1.9 g, yield: 90%

Sources & evidence

ORD record
ord-ae3605cf9a9b400aaff0c19b92126691
Source dataset
uspto-grants-2016_02
Patent number
US09249084B2

Reaction notes

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