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Aluminium lithium hydride → 4-Benzyl-1-[2-(2-fluorophenyl)propyl]piperazine

HRID 1600838
Notes
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Reaction equation

HRID 1600838 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][N:17]([C:20](=O)[CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[CH3:22])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[CH3:22])[CH2:18][CH2:19]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 218308564-Benzyl-1-[2-(2-fluorophenyl)propanoyl]piperazine

Product 1

HCID 218308454-Benzyl-1-[2-(2-fluorophenyl)propyl]piperazineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (1M, 34 ml) was added dropwise over 15 min to a 0° C. solution of 4-benzyl-1-[2-(2-fluorophenyl)propanoyl]piperazine (5.54 g, 0.017 mol) in THF (150 ml). The reaction mixture was stirred at 0° C. for 10 min and at room temperature for 24 h, cooled to 0° C. and quenched with water (1.6 ml), 4N NaOH (1.6 ml) and water (4.5 ml). The solid was filtered off through celite and the filtrate evaporated. Chromatography on silica gel with dichloromethane-methanol (99:1) yielded 4-benzyl-1-[2-(2-fluorophenyl)propyl]piperazine (3.17 g, 60%) as a colourless oil.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with water (1.6 ml), 4N NaOH (1.6 ml) and water (4.5 ml)
  3. filtrationThe solid was filtered off through celite
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-8ff197f7851a4a92b26ae333297bbad0
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05977116

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes