Aluminium lithium hydride → 1-[2-(4-Fluorophenyl)-2-(1-isopropylpiperidin-4-yl)ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazine

HRID 497349Notes

Reaction equation

HRID 497349 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH:10]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH: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)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.CCOCC.N>[F:41][C:38]1[CH:37]=[CH:36][C:35]([CH:10]([CH:7]2[CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:9][CH2:8]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:40][CH:39]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 223186581-Isopropyl-4-(1-(4-fluorophenyl)-2-{4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazin-1-yl}-2-oxoethyl)piperidine

Product 1

HCID 223186351-[2-(4-Fluorophenyl)-2-(1-isopropylpiperidin-4-yl)ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazineYield 95.2%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

0.14 g of 1-Isopropyl-4-(1-(4-fluorophenyl)-2-{4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazin-1-yl}-2-oxoethyl)piperidine was dissolved in 5 ml of tetrahydrofuran, and 10 ml of lithium aluminum hydride was added, followed 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-(1-isopropylpiperidin-4-yl)ethyl]-4-[4-(2-methoxynaphthalen-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-91401aa67ff54ce689c74766e5e7967b
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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