Aluminium lithium hydride → 1-[2-(4-Fluorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)ethyl]-4-(4-naphthalen-1-yl-butyl)piperazine

HRID 497347Notes

Reaction equation

HRID 497347 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:31]2[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH:36]=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:3]=[CH:4][C:5]([CH:8]([C:31]2[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH:36]=2)[CH2:9][N:11]2[CH2:12][CH2:13][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)[CH2:15][CH2:16]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 223186454-{1-(4-fluorophenyl)-2-[4-(4-naphthalen-1-yl-butyl)piperazin-1-yl]-2-oxoethyl}-1-methyl-3,6-dihydro-2H-pyridine

Product 1

HCID 223186661-[2-(4-Fluorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)ethyl]-4-(4-naphthalen-1-yl-butyl)piperazineYield 41.2%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

0.25 g of 4-{1-(4-Fluorophenyl)-2-[4-(4-naphthalen-1-yl-butyl)piperazin-1-yl]-2-oxoethyl}-1-methyl-3,6-dihydro-2H-pyridine 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 0.10 g of 1-[2-(4-fluorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)ethyl]-4-(4-naphthalen-1-yl-butyl)piperazine 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-0134119ef3e6475eb53fa360e15ef9b9
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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