Hydrochloric Acid → Atomoxetine hydrochloride

HRID 2116887Notes

Reaction equation

HRID 2116887 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 room temperature with 25.5 ml of n-butyl acetate and 0.6 ml of toluene under stirring. Keeping the temperature between about 18° C. and about 20° C. by means of water-ice bath cooling, 1.4 g of aqueous (36.4% w/w) hydrogen chloride was added into the obtained slurry. The slurry was stirred for 1 hour at room temperature. The solid was collected by filtration, washed with 6 ml of n-butyl acetate and dried in vacuo at 65° C.

Workup

  1. customthe temperature between about 18° C. and about 20° C.
  2. temperaturecooling
  3. stirringThe slurry was stirred for 1 hour at room temperature
  4. filtrationThe solid was collected by filtration
  5. washwashed with 6 ml of n-butyl acetate
  6. customdried in vacuo at 65° C.

Sources & evidence

ORD record
ord-cd216dd62f374b419396b6a1ab86234d
Source dataset
uspto-grants-2008_10
Patent number
US07439399B2

Reaction notes

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