Water → HCID 13151526, compound

HRID 1648874Notes

Reaction equation

HRID 1648874 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH:11]([CH2:13]I)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[C:15]1([N:21]2[C:25]3([CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:24](=[O:31])[NH:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:32](=[O:35])([O-:34])[O-].[K+].[K+].O>CN(C)C=O>[C:8]([OH:31])(=[O:9])/[CH:12]=[CH:11]\[C:32]([OH:34])=[O:35].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH:11]([CH2:13][N:28]3[CH2:27][CH2:26][C:25]4([N:21]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)[CH2:22][NH:23][C:24]4=[O:31])[CH2:30][CH2:29]3)[CH2:10][O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 131514992-(4-Fluorophenyl)-4-(iodomethyl)tetrahydrofuran

Product 1

HCID 13151526HCID 13151526, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.2 g of 2-(4-fluorophenyl)-4-(iodomethyl)tetrahydrofuran, 2.4 g of 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one and 1.4 g of potassium carbonate in 60 ml of dimethylformamide is heated with stirring at 70° C. for 21 hours. The reaction mixture is then poured into water and extracted with ethyl acetate. The extract is washed with water and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by column chromatography on silica gel with chloroform eluant. The thus obtained purified crystals are treated with maleic acid and recrystallized from ethanol-water to give 8-[2-(4-fluorophenyl)-tetrahydro-4-furylmethyl]-1-phenyl-1,3,8-triazaspiro[4.5]-decan-4-one maleate, melting at 175° C. with decomposition.

Workup

  1. temperatureis heated
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel with chloroform eluant
  7. customThe thus obtained
  8. custompurified crystals
  9. additionare treated with maleic acid
  10. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-adb25b651dc846c396321983accbd9e2
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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