Sodium Iodide → HCID 18959738, compound

HRID 1197949Notes

Reaction equation

HRID 1197949 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:13][C:12]2=[O:25].OC1C=C2C(=CC=1)OC(C1C=CC=CC=1)=CC2=O.BrCCCCCCCl.ClCCCCOC1C=C2C(=CC=1)OC(C1C=CC=CC=1)=CC2=O.[OH:75][CH2:76][CH2:77][CH:78]1[CH2:83][CH2:82][NH:81][CH2:80][CH2:79]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[ClH:1].[OH:75][CH2:76][CH2:77][CH:78]1[CH2:83][CH2:82][N:81]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:18]=[CH:17][C:16]3[O:15][C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:13][C:12](=[O:25])[C:11]=3[CH:10]=2)[CH2:80][CH2:79]1

Participants

10

Reactant 7

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 722796-HydroxyflavoneHCID 739534-PiperidineethanolHCID 805161-Bromo-6-chlorohexaneHCID 14982937HCID 14982937, compoundHCID 14982939HCID 14982939, compound

Product 1

HCID 18959738HCID 18959738, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(6-chlorohexoxy)flavone (Prepared from 6-hydroxyflavone and 1-bromo-6-chlorohexane by a manner similar to 6-(4-chlorobutoxy)flavone described in Example 1.) (2.00 g, 5.6 mmol), 4-(2-hydroxyethyl)piperidine (1.09 g, 8.4 mmol), sodium iodide (0.92 g, 6.1 mmol), and potassium carbonate (1.16 g, 8.4 mmol) in anhydrous DMF was stirred at 80°-90° C. for 24 hours. The reaction was cooled to room temperature and water (300 mL) was added to the flask. The resulting precipitate was collected by filtration and dissolved in methylene chloride (350 mL). This solution was washed with water (2×150 mL), brine (2×150 mL) and then the solution was dried over sodium sulfate. Removal of the solvent gave 2.32 g of the free base. The free base was dissolved in hot EtOAc and the solution filtered. Then 1 equivalent of a 1M anhydrous solution of HCl in ether (Aldrich Chemical Co.) was added. The mixture was cooled in the freezer for 1 hour and the resulting solid was collected by vacuum filtration and recrystallized from methyl alcohol to give 6-[6-(4-(2-hydroxyethyl)piperidylhexoxy)]flavone hydrochloride which was dried over P205 in high vacuum at 100° C. (yield=2.29 g, 76%): mp 204°-206° C.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. dissolutiondissolved in methylene chloride (350 mL)
  3. washThis solution was washed with water (2×150 mL), brine (2×150 mL)
  4. dry with materialthe solution was dried over sodium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-fe94ec26d53643d78ed6b1b403c225dd
Source dataset
uspto-grants-1994_01
Patent number
US05278174

Reaction notes

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