Boron tribromide → HCID 22718253, compound

HRID 1582753Notes

Reaction equation

HRID 1582753 reaction equation
[C:1]([C:3]([C:26]1[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=1)([CH:23]([CH3:25])[CH3:24])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:9][CH2:8]1)#[N:2].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([C:3]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)([CH:23]([CH3:25])[CH3:24])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:9][CH2:8]1)#[N:2]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 9868531HCID 9868531, compound

Product 1

HCID 22718253HCID 22718253, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-Cyano-5-methyl-4-(4-methoxyphenyl)hexyl]-4-[2-(4-fluorophenoxy)ethyl]piperazine 85 mg obtained in Example 11 was dissolved in dichloromethane 3 ml, and 1M-boron tribromide (dichloromethane solution, 0.5 ml) was added dropwise thereto under ice-cooling. After haeting the mixture under reflux for 5 hours, it was cooled to room temperature and basified with aqueous saturated sodium bicarbonate under ice-cooling. The mixture was extracted with ethyl acetate, and the organic layer was washed with water, dried over sodium sulfate anhydride, and evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 30 mg, 36% was obtained as a colorless oil.

Workup

  1. temperatureunder ice-cooling
  2. temperatureunder reflux for 5 hours
  3. temperaturecooling
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materialdried over sodium sulfate anhydride
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 30 mg, 36%
  9. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-f3e9764ba0f840b2b709a98bf33e7858
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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