Hydrogen iodide → 3-(1-(Dimethylamino)-2-methylpentan-3-yl)phenol

HRID 533682Notes

Reaction equation

HRID 533682 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:16][CH3:17])[CH:10]([CH3:15])[CH2:11][N:12]([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.I>>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:16][CH3:17])[CH:10]([CH3:15])[CH2:11][N:12]([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 24841Hydrogen iodideHCID 223770203-(3-methoxy-phenyl)-N,N,2-trimethyl pentylamine

Product 1

HCID 64330913-(1-(Dimethylamino)-2-methylpentan-3-yl)phenol

Procedure

The steps are: add 3-(3-methoxy-phenyl)-N,N,2-trimethyl pentylamine into a reaction flask, add hydroiodic acid, and perform heating and reflux for 5 hours; detect the reaction process by TLC; after that, cool the resultant to the room temperature, pour it to an alkaline solution to make the pH become 9, perform extraction by ethyl acetate and rinse by water; recycle the solvent by drying and decompression to obtain a light yellow liquid, 3-(3-hydroxy-phenyl)-N,N,2-trimethyl pentylamine; and separate the mother solution by a separator, form the salt by the acidification of hydrochloric acid to obtain tapentadol hydrochloride. HPLC: 99.56%, ee %>99.5%.

Workup

  1. temperatureperform heating
  2. temperaturereflux for 5 hours
  3. additionpour it to an alkaline solution
  4. extractionextraction by ethyl acetate
  5. washrinse by water
  6. customby drying

Sources & evidence

ORD record
ord-3f7dc252fecc47a2b4745d303d18698a
Source dataset
uspto-grants-2014_10
Patent number
US08853393B2

Reaction notes

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