Potassium Carbonate → 7-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-{9-[4-(4,4,5,5,5-pentafluoropentyl)piperazinyl]nonyl}-3-methylchroman

HRID 1792290Notes

Reaction equation

HRID 1792290 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:18][CH:17]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[F:47][C:48]([F:67])([C:63]([F:66])([F:65])[F:64])[CH2:49][CH2:50][CH2:51]OS(C1C=CC(C)=CC=1)(=O)=O>O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][N:38]([CH2:51][CH2:50][CH2:49][C:48]([F:67])([F:47])[C:63]([F:66])([F:65])[F:64])[CH2:39][CH2:40]3)[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:18][CH:17]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 220330274,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonateHCID 220331067-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-(9-piperazinylnonyl)-3-methylchroman

Product 1

HCID 220332377-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-{9-[4-(4,4,5,5,5-pentafluoropentyl)piperazinyl]nonyl}-3-methylchromanYield 48.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-(9-piperazinylnonyl)-3-methylchroman (380 mg, 0.685 mmol), K2CO3 (190 mg, 1.375 mmol) and 4,4,5,5,5-pentafluoropentyl-4-methylbenzenesulfonate (460 mg, 1.384 mmol) were refluxed under acetone for 15 hours. After the mixture was cooled down to room temperature, water was added thereto, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the organic solvent was removed under reduced pressure. The concentrate was subjected to column chromatography (n-hexane:ethyl acetate=4:1) to give 238 mg (yield: 48%) of the title compound as a white solid.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b65e146e05a14a1a8dfc125bbb52583a
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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