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

HRID 1600838Notes

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

Participants

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

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