Hydrochloric Acid → Atomoxetine hydrochloride

HRID 2116883Notes

Reaction equation

HRID 2116883 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[O:9][C@@H:10]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:11][CH2:12][NH:13][CH3:14]>C(OCCCC)(=O)C>[ClH:1].[CH3:14][NH:13][CH2:12][CH2:11][C@@H:10]([O:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:2])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54841Atomoxetine

Product 1

HCID 54840Atomoxetine hydrochlorideYield 99.8%

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent

Procedure

Under stirring and maintaining temperature between 22° C. and 25° C. by means of water bath cooling, 10.07 g (0.09945 mol) of aqueous hydrogen chloride (36%) were dropped on 177 g (0.08648 mol) of atomoxetine base solution (n-butyl acetate), prepared as in Example 7. The hydrochloride then crystallized. The obtained suspension was stirred at about 25° C. for one hour. The solid was collected by filtration and washed twice with 30 ml of n-butyl acetate each time. The solid collected was dried for 18 hours at 70° C. under vacuum. Tomoxetine hydrochloride content: >99% by HPLC assay. Weight: 25.18 g (0.08629 mol). Yield: 99.8%. Atomoxetine hydrochloride enantiomeric ratio: R/S>99/1 (by chiral HPLC)

Workup

  1. temperaturemaintaining temperature between 22° C. and 25° C. by means of water bath
  2. temperaturecooling
  3. customThe hydrochloride then crystallized
  4. stirringThe obtained suspension was stirred at about 25° C. for one hour
  5. filtrationThe solid was collected by filtration
  6. washwashed twice with 30 ml of n-butyl acetate each time
  7. customThe solid collected
  8. customwas dried for 18 hours at 70° C. under vacuum

Sources & evidence

ORD record
ord-e27f3af8d59543bfa09d479b5eacdfce
Source dataset
uspto-grants-2008_10
Patent number
US07439399B2

Reaction notes

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