Potassium Iodide → DES(6-fluoro-1,2-benzoxazole)-2,4-difluorobenzoyl risperidone

HRID 969735

Reaction equation

HRID 969735 reaction equation
Cl.[F:2][C:3]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:4]=1[C:5]([CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:6].Cl[CH2:19][CH2:20][C:21]1[C:26](=[O:27])[N:25]2[CH2:28][CH2:29][CH2:30][CH2:31][C:24]2=[N:23][C:22]=1[CH3:32].C(=O)([O-])O.[Na+].[I-].[K+]>O.C(#N)C>[F:2][C:3]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:4]=1[C:5]([CH:7]1[CH2:8][CH2:9][N:10]([CH2:19][CH2:20][C:21]2[C:26](=[O:27])[N:25]3[CH2:28][CH2:29][CH2:30][CH2:31][C:24]3=[N:23][C:22]=2[CH3:32])[CH2:11][CH2:12]1)=[O:6]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 27630793-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4hpyrido(1,2-a)pyrimidin-4-oneHCID 18759874(2,4-Difluorophenyl)(piperidin-4-yl)methanone--hydrogen chloride (1/1)

Product 1

HCID 29941101DES(6-fluoro-1,2-benzoxazole)-2,4-difluorobenzoyl risperidone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 29.2 g (0.1116 mole) of 4-(2,4-difluoro-benzoyl)-piperidine-hydrochloride, 25.3 g (0.1117 mole) of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 500 ml of acetonitrile, 19.6 g (0.2333 mole) of sodium hydrogencarbonate and 0.25 g (0.0015 mole) of potassium iodide is heated to boiling for 10 hours with stirring. The reaction mixture is cooled to room temperature, to the residue 200 ml of water are added. The mixture is stirred for 30 minutes and extracted with 200 ml of dichloromethane. The organic phase is separated, dried over magnesium sulfate, filtered and the filtrate is evaporated. The oily residue thus obtained is purified as follows:

Workup

  1. temperatureis heated
  2. additionare added
  3. stirringThe mixture is stirred for 30 minutes
  4. extractionextracted with 200 ml of dichloromethane
  5. customThe organic phase is separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated
  9. customThe oily residue thus obtained
  10. customis purified

Sources & evidence

ORD record
ord-12fc39fc25a4411fbc84b164281c31d8
Source dataset
uspto-grants-2007_12
Patent number
US07307168B2

Linked notes

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