Hydrochloric Acid → Fluoxetine hydrochloride

HRID 1761286Notes

Reaction equation

HRID 1761286 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1.C(OCC)C.[ClH:28].C(OCC)(=O)C>CCCCCC>[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:15][CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1.[ClH:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 3386FluoxetineHCID 8857Ethyl Acetate

Product 1

HCID 62857Fluoxetine hydrochlorideYield 107.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a 3.0 L round bottom flask is added 25.5 g (0.0824 mol) of fluoxetine free base. To this is added 850 mL of diethyl ether and the amine is dissolved. To this solution is added 150 mL of an ethereal hydrochloric acid solution (0.069 mol HCl/100 mL). The reaction is stirred for 30 minutes and then the ether is rotoevaporated to dryness. The solid was taken up in a minimum of ethyl acetate and hexane was added until crystals started forming. The white solid is placed in the refrigerator for 14 hours at about 5° C. The solution was filtered and dried to give 25.75 g of fluoxetine hydrochloride.

Workup

  1. additionwas added until crystals
  2. customstarted forming
  3. waitThe white solid is placed in the refrigerator for 14 hours at about 5° C
  4. filtrationThe solution was filtered
  5. customdried

Sources & evidence

ORD record
ord-dcbfcdbc6b7b4045bb79a95a3eeac3a8
Source dataset
uspto-grants-2005_01
Patent number
US06846957B2

Reaction notes

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