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Potassium Iodide → Paliperidone Tetradehydro Impurity

HRID 448544
Notes
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Reaction equation

HRID 448544 reaction equation
Cl.Cl[CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:8]2=[N:7][C:6]=1[CH3:17].Cl.[F:19][C:20]1[CH:34]=[CH:33][C:23]2[C:24]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[N:25][O:26][C:22]=2[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(#N)C>[F:19][C:20]1[CH:34]=[CH:33][C:23]2[C:24]([CH:27]3[CH2:28][CH2:29][N:30]([CH2:3][CH2:4][C:5]4[C:10](=[O:11])[N:9]5[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:8]5=[N:7][C:6]=4[CH3:17])[CH2:31][CH2:32]3)=[N:25][O:26][C:22]=2[CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11334359R-56109 hydrochlorideHCID 250093164H-Pyrido[1,2-a]pyrimidin-4-one, 3-(2-chloroethyl)-9-hydroxy-2-methyl-, hydrochloride

Product 1

HCID 44602517Paliperidone Tetradehydro Impurity

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
82.5 °C

Procedure

A mixture of 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one hydrochloride (formula-5) (11.1 grams), 6-fluoro-3-(4-piperidinyl)-1,2-benzoisoxazole mono hydrochloride (formula-6) (10 grams), sodium carbonate (7.5 grams), potassium iodide (0.64 grams) in acetonitrile (100 ml) was heated to 80-85° C. The reaction mixture was refluxed for 17 hrs under nitrogen. Then it was cooled to −10° C. and stirred for 30 min. The solid obtained was filtered and washed with chilled acetonitrile. The solid was taken in water and treated with sodiumhydrosulphite (hydrose) (2.0 grams). The solid was filtered and washed with water and dried at 50° C. to provide the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 17 hrs under nitrogen
  2. temperatureThen it was cooled to −10° C.
  3. customThe solid obtained
  4. filtrationwas filtered
  5. washwashed with chilled acetonitrile
  6. additiontreated with sodiumhydrosulphite (hydrose) (2.0 grams)
  7. filtrationThe solid was filtered
  8. washwashed with water
  9. customdried at 50° C.

Sources & evidence

ORD record
ord-c5ea3a6f858943d5b13ac4b15dff9dcd
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08481729B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes