4-(1-(4-Fluorophenyl)-2-{4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazin-1-yl}-2-oxoethyl)piperidine dihydrochloride → 1-[2-(4-Fluorophenyl)-2-piperidin-4-yl-ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazine

HRID 497340Notes

Reaction equation

HRID 497340 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[C:11]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][C:24]=3[O:33][CH3:34])[CH2:15][CH2:14]2)=O)=[CH:6][CH:5]=1>[OH-].[Na+]>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:35]2[CH2:36][CH2:37][NH:38][CH2:39][CH2:40]2)[CH2:11][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][C:24]=3[O:33][CH3:34])[CH2:15][CH2:14]2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 223186484-(1-(4-Fluorophenyl)-2-{4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazin-1-yl}-2-oxoethyl)piperidine dihydrochloride

Product 1

HCID 223186651-[2-(4-Fluorophenyl)-2-piperidin-4-yl-ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazineYield 101.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

0.15 g of 4-(1-(4-Fluorophenyl)-2-{4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazin-1-yl}-2-oxoethyl)piperidine dihydrochloride was dissolved in 1M aqueous sodium hydroxide solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was dissolved in 5 ml of tetrahydrofuran, and 10 mg lithium aluminum hydride was added, followed by stirring at 50° C. for 15 minutes. The reaction solution was cooled to room temperature and diluted with ether, and 25% aqueous ammonia solution was added dropwise. The precipitate was removed by Celite filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by a silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=4:1) to give 0.13 g of 1-[2-(4-fluorophenyl)-2-piperidin-4-yl-ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazine as an oil.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customAfter removal of the drying agent
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 5 ml of tetrahydrofuran
  7. addition10 mg lithium aluminum hydride was added
  8. temperatureThe reaction solution was cooled to room temperature
  9. additiondiluted with ether, and 25% aqueous ammonia solution
  10. additionwas added dropwise
  11. customThe precipitate was removed by Celite filtration
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customthe residue was purified by a silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1c9ffd5b716843b98c2f253ffa3306cd
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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