Hydrochloric Acid → Atomoxetine hydrochloride

HRID 2116885Notes

Reaction equation

HRID 2116885 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[O:8][C@@H:9]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:10][CH2:11][NH:12][CH3:13].C([O-])(=O)[C@H](C1C=CC=CC=1)O.C1(C)C=CC=CC=1.[ClH:38]>CO>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[O:8][C@@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][CH2:11][NH:12][CH3:13].[ClH:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 131727128HCID 131727128, compound

Product 1

HCID 54840Atomoxetine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Two grams (0.00491 mol) of atomoxetine (S)-(+)-mandelate was mixed at room temperature with 10 ml of toluene and 1 ml of MeOH and under stirring were heated at 60° C. Keeping the temperature at 60° C. by means of oil bath heating, 0.58 g of aqueous (37%) hydrogen chloride was dropped into the obtained solution. The solution was cooled and at 20-25° C. a solid crystallized. The slurry was stirred for 1 hour at 0° C., then the solid was collected by filtration, washed with toluene and dried under vacuum at 45° C. for 5 hours.

Workup

  1. customat 60° C.
  2. temperatureheating
  3. temperatureThe solution was cooled and at 20-25° C. a solid
  4. customcrystallized
  5. stirringThe slurry was stirred for 1 hour at 0° C.
  6. filtrationthe solid was collected by filtration
  7. washwashed with toluene
  8. customdried under vacuum at 45° C. for 5 hours

Sources & evidence

ORD record
ord-9eac1b53bca24230923e5e51b11fbf23
Source dataset
uspto-grants-2008_10
Patent number
US07439399B2

Reaction notes

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