Potassium Hydroxide → Paroxetine

HRID 2119784Notes

Reaction equation

HRID 2119784 reaction equation
[CH:1]1[C:6]([C@H:7]2[C@H:12]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]4[O:23][CH2:22][O:21][C:19]=4[CH:20]=3)[CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:5][CH:4]=[C:3]([F:24])[CH:2]=1.C1(NC(=O)[O-])C=CC=CC=1.[OH-].[K+]>C1(C)C=CC=CC=1>[CH:5]1[C:6]([C@H:7]2[C@H:12]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]4[O:23][CH2:22][O:21][C:19]=4[CH:20]=3)[CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:1][CH:2]=[C:3]([F:24])[CH:4]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86586157HCID 86586157, compound

Product 1

HCID 43815Paroxetine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

A common procedure is disclosed in EP223403, and corresponding U.S. Pat. No. 4,721,723, wherein a solid-state paroxetine phenylcarbamate (3) was dissolved in toluene and KOH was added. The mixture was refluxed for 2 hours with good agitation. The slurry was then cooled to 20° C. and the toluene washed with water. The obtained solution of paroxetine free base in toluene was further treated with HCI to isolate paroxetine in a form of its hydrochloride salt. Similar procedures for the synthesis of paroxetine and various salts of paroxetine have been disclosed in WO 99-32484, GB 2336364, WO 99-52901, WO 00-39090 and WO 00-32594.

Workup

  1. temperatureThe mixture was refluxed for 2 hours with good agitation
  2. washthe toluene washed with water
  3. additionThe obtained solution of paroxetine free base in toluene was further treated with HCI

Sources & evidence

ORD record
ord-1d44880b4e334a1d9e7452bb7c488286
Source dataset
uspto-grants-2004_02
Patent number
US06686473B2

Reaction notes

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