Hydrochloric Acid → Atomoxetine hydrochloride

HRID 2099918Notes

Reaction equation

HRID 2099918 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>[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:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][CH2:12][NH:13][CH3:14].[ClH:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54841Atomoxetine

Product 1

HCID 54840Atomoxetine hydrochlorideYield 122.4%

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent

Procedure

Under stirring, while maintaining the temperature between about 22° C. and about 25° C. with a water bath, 286 g (2.825 mol) of aqueous hydrogen chloride (36%) are dropped on 5063 g (2.379 mol) of Atomoxetine base in a solution of n-butyl acetate, prepared as described in U.S. Provisional Applications Nos. 60/583643, 60/583644, and 60/622065. The hydrochloride crystallized. The resulting suspension is stirred at about 25° C. for about one hour, and the solid is collected by filtration, and washed three times with 900 ml of n-butyl acetate. About 850 g of wet Atomoxetine Hydrochloride are obtained. After two separate preparations, samples of obtained wet solids are dissolved in water (2 g in 100 ml). The pH determined for each sample is 2.39 and pH 2.40, respectively.

Workup

  1. temperaturewhile maintaining the temperature between about 22° C. and about 25° C. with a water bath
  2. customprepared
  3. customThe hydrochloride crystallized
  4. stirringThe resulting suspension is stirred at about 25° C. for about one hour
  5. filtrationthe solid is collected by filtration
  6. washwashed three times with 900 ml of n-butyl acetate

Sources & evidence

ORD record
ord-09ffef65b06c448195a3b65d6e54f90f
Source dataset
uspto-grants-2009_08
Patent number
US07569729B2

Reaction notes

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