4-{1-(4-Fluorophenyl)-2-[4-(naphthalen-1-yl-butyl)piperazin-1-yl]-2-oxoethyl}-1-methylpiperidin-4-ol → 4-{1-(4-Fluorophenyl)-2-[4-(naphthalen-1-yl-butyl)piperazin-1-yl]ethyl}-1-methylpiperidin-4-ol

HRID 497343Notes

Reaction equation

HRID 497343 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:31]2([OH:38])[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.CCOCC.N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:31]2([OH:38])[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]2)[CH2:9][N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 178506574-{1-(4-Fluorophenyl)-2-[4-(naphthalen-1-yl-butyl)piperazin-1-yl]-2-oxoethyl}-1-methylpiperidin-4-olHCID 21226445Aluminium lithium hydride

Product 1

HCID 178506544-{1-(4-Fluorophenyl)-2-[4-(naphthalen-1-yl-butyl)piperazin-1-yl]ethyl}-1-methylpiperidin-4-olYield 13.6%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

0.25 g of 4-{1-(4-Fluorophenyl)-2-[4-(naphthalen-1-yl-butyl)piperazin-1-yl]-2-oxoethyl}-1-methylpiperidin-4-ol was dissolved in 3 ml of tetrahydrofuran, and 18 mg of 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 33 mg of 4-{1-(4-fluorophenyl)-2-[4-(naphthalen-1-yl-butyl)piperazin-1-yl]ethyl}-1-methylpiperidin-4-ol as an oil.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. additionwas added dropwise
  3. customThe precipitate was removed by Celite filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by a silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-a0bbc6576d2841f68de2867174dee390
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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