Hexane → HCID 22033064, compound

HRID 1792294Notes

Reaction equation

HRID 1792294 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH2:22][O:23][CH3:24])=[CH:18][CH:19]=3)[O:14][CH2:13][C:12]2([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=2)[CH3:25])=[CH:7][CH:6]=1.[C:36]([C:40]1[CH:41]=[C:42]([CH2:50][N:51]2[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)[CH:43]=[C:44]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:45]=1)([CH3:39])([CH3:38])[CH3:37].C(=O)([O-])[O-].[K+].[K+].CCCCCC>CC(C)=O.CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[C:36]([C:40]1[CH:41]=[C:42]([CH2:50][N:51]2[CH2:52][CH2:53][N:54]([CH2:2][CH2:3][O:4][C:5]3[CH:10]=[CH:9][C:8]([CH:11]4[C:20]5[C:15](=[CH:16][C:17]([O:21][CH2:22][O:23][CH3:24])=[CH:18][CH:19]=5)[O:14][CH2:13][C:12]4([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=4)[CH3:25])=[CH:7][CH:6]=3)[CH2:55][CH2:56]2)[CH:43]=[C:44]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:45]=1)([CH3:37])([CH3:38])[CH3:39]

Participants

9

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 18770224HCID 18770224, compoundHCID 22033222HCID 22033222, compound

Product 1

HCID 22033064HCID 22033064, compoundYield 51%

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3RS,4SR)-4-[4-(2-Chloroethoxy)phenyl]-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methylchroman (210 mg, 0.42 mmol) and {(3,5-bis(t-butyl)phenyl]methyl}piperazine (243 mg, 0.84 mmol) were dissolved in a solvent mixture of acetone (4 ml) and DMF (0.4 ml). To the mixture potassium carbonate (116 mg, 0.84 mmol) and tetrabutylammonium iodide (16 mg, 0.04 mmol) added were, and the mixture was stirred while heated under reflux for 3 days. The reaction solution was extracted with ethyl acetate, dried over sodium sulfate, and filtered. The filtrate was evaporated under reduced pressure, and the concentrate thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 160 mg (yield: 51%) of a white foamy solid.

Workup

  1. temperaturewhile heated
  2. temperatureunder reflux for 3 days
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. concentrationthe concentrate thus
  8. customobtained

Sources & evidence

ORD record
ord-4b404b72e8764ac39f42611c05e23403
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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