Hydrochloric Acid → Atomoxetine hydrochloride

HRID 2116888Notes

Reaction equation

HRID 2116888 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.C(OCCCC)(=O)C.[ClH:39]>C1(C)C=CC=CC=1>[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:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31272Butyl AcetateHCID 131727128HCID 131727128, compound

Product 1

HCID 54840Atomoxetine hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Atomoxetine (S)-(+)-mandelate (5.17 g, 0.01267 mol) was mixed at about 50° C. with 25.5 ml of n-butyl acetate and 0.6 ml of toluene under stirring. Keeping the temperature at 50° C. by means of oil bath heating, 1.4 g of aqueous (36.4% w/w) hydrogen chloride was added into the obtained slurry. The slurry that formed was cooled at room temperature and stirred for 1 hour. The solid was collected by filtration, washed with 6 ml of n-butyl acetate and dried in vacuo at 45° C.

Workup

  1. customat 50° C.
  2. temperatureheating
  3. customThe slurry that formed
  4. stirringstirred for 1 hour
  5. filtrationThe solid was collected by filtration
  6. washwashed with 6 ml of n-butyl acetate
  7. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-537a5f5f8dcc42c3b2d22f47ba95a19c
Source dataset
uspto-grants-2008_10
Patent number
US07439399B2

Reaction notes

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