[4-(4-Benzylpiperazin-1-yl)phenyl]methanol → [4-(Piperazin-1-yl)phenyl]methanol

HRID 1760922Notes

Reaction equation

HRID 1760922 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CCO.[Pd]>[N:11]1([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][OH:21])=[CH:18][CH:19]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 22593960[4-(4-Benzylpiperazin-1-yl)phenyl]methanol

Product 1

HCID 22594064[4-(Piperazin-1-yl)phenyl]methanolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of [4-(4-Benzyl-piperazin-1-yl)-phenyl]-methanol in EtOH (50 ml) under a blanket of argon was added a suspension of 10% palladium on charcoal (1.5 g) in EtOH (150 ml). Hydrogen was bubbled through the suspension for 1 h and then the reaction mixture was stirred under a blanket of hydrogen for 60 h at RT. The catalyst was filtered off and the solvent removed in vacuo to yield the title compound as a white solid (4.8 g, 100%). 1H-NMR δ (CDCl3) 7.30-7.21 (2H, m, ArH), 6.94-6.88 (2H, m, ArH), 4.59 (2H, s), 3.18-2.98 (8H, m). HPLC: 0.5 min (37% @ 214 nm), 0.7 min (55% @ 214 nm), multiple peaks due to salt formation from TFA buffer; LRMS +ve: 193 (M+1, 70).

Workup

  1. customHydrogen was bubbled through the suspension for 1 h
  2. filtrationThe catalyst was filtered off
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4751caede2fa43f9925b287bc483e01c
Source dataset
uspto-grants-2005_01
Patent number
US06846825B1

Reaction notes

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