Potassium Carbonate → HCID 178456386, compound

HRID 1984037Notes

Reaction equation

HRID 1984037 reaction equation
I[C:2]1[CH:25]=[CH:24][C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH:10]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]3)=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C:27]1=[O:32].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.[Cu]>[CH:21]([N:18]1[CH2:19][CH2:20][N:15]([C:13]([C@H:10]2[CH2:11][CH2:12][C@H:7]([O:6][C:5]3[CH:24]=[CH:25][C:2]([N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][C:27]4=[O:32])=[CH:3][CH:4]=3)[CH2:8][CH2:9]2)=[O:14])[CH2:16][CH2:17]1)([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 126652-PiperidoneHCID 68443233HCID 68443233, compound

Product 1

HCID 178456386HCID 178456386, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1.04 g (4.09 mmol) of cis-(4-isopropyl-piperazin-1-yl)-(4-hydroxy-cyclohexyl)-methanone, 1.50 g (6.82 mmol) of 4-iodephenol, 1.25 g (4.77 mmol) of triphenylphisphine in 5 ml THF, 1.1 g (4.78 mmol) of di-tert-butyl azodicarboxylate was added at 0° C., and stirred for 12 h at room temperature. After evaporation, the residue was purified by column chromatography on silica gel eluting with cyclohexane and ethyl acetate=from 100:0 to 2:1. The combined product fractions were evaporated to dryness to yield 0.67 g (14% yields, about 67% purity) of [4-(4-iodo-phenoxy)-cyclohexyl]-(4-isopropyl-piperazin-1-yl)-methanone. A mixture 100 mg (0.15 mmol) of [4-(4-iodo-phenoxy)-cyclohexyl]-(4-isopropyl-piperazin-1-yl)-methanone, 87 mg (0.88 mmol) of 2-piperidone, 41 mg (0.3 mmol) of potassium carbonate and 37 mg (0.58 mmol) of copper was stirred at 175 degree for 6 hr. The mixture was diluted with AcOEt, filtered through celite. The filtrate was washed with saturated NaHCO3 solution and brine, dried over MgSO4, and evaporated. The residue was purified by column chromatography on silica eluting with cyclohexane and ethyl acetate=from 100:0 to 1:3. The combined product fractions were evaporated to dryness to yield 30 mg (32%) of the title compound. MS (m/e): 428.3 (MH+).

Workup

  1. filtrationfiltered through celite
  2. washThe filtrate was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica eluting with cyclohexane and ethyl acetate=from 100:0 to 1:3
  6. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-39587347bd9040eea83ce3a057a0c3b5
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

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