Water → HCID 22248512, compound

HRID 914918Notes

Reaction equation

HRID 914918 reaction equation
C[O:2][C:3]1[C:4]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([C:17](=[O:26])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[CH2:13][CH2:12]2)=[N:5][CH:6]=[C:7]([CH3:9])[N:8]=1.O>ClCCl.I[Si](C)(C)C>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][C:17]([CH:14]1[CH2:13][CH2:12][N:11]([CH2:10][C:4]2[C:3](=[O:2])[NH:8][C:7]([CH3:9])=[CH:6][N:5]=2)[CH2:16][CH2:15]1)=[O:26]

Participants

5

Reactant 2

HCID 962WaterHCID 22247971HCID 22247971, compound

Product 1

HCID 22248512HCID 22248512, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 85247Trimethylsilyl iodideSolvent2×

Procedure

After dissolving 352 mg of 1-[(1-(3-methoxy-5-methyl-2-pyrazinylmethyl)piperidin-4-yl]-2-(2-fluorophenyl)ethanone in 3 ml of dichloromethane, 0.5 ml of iodotrimethylsilane was added and the mixture was stirred for 45 minutes at room temperature. Next, 2 ml of iodotrimethylsilane was added and the mixture was further stirred for 2 hours at room temperature. Water was added to the reaction solution, the mixture was rendered alkaline with sodium carbonate, and extraction was performed with dichloromethane. The extract was dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol). Diethyl ether was added and the mixture was filtered to obtain the title compound (92 mg, 27% yield).

Workup

  1. additionwas added
  2. stirringthe mixture was further stirred for 2 hours at room temperature
  3. extractionwith sodium carbonate, and extraction
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol)
  7. additionDiethyl ether was added
  8. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-471a423cb2314cdf815c1e211d475f97
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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