4-(4-Benzylpiperazin-1-yl)-2-chloropyrimidine → 4-(Piperazin-1-yl)pyrimidine

HRID 1782736Notes

Reaction equation

HRID 1782736 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11](CC3C=CC=CC=3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[H][H]>C(O)C.[Pd]>[N:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:7][CH:2]=1

Participants

5

Reactant 2

HCID 183213004-(4-Benzylpiperazin-1-yl)-2-chloropyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 183211374-(Piperazin-1-yl)pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 7.4 g (0.0256 mol) of 1-(2-chloro-4-pyrimidinyl)-4-(phenylmethyl)piperazine in 100 ml of ethanol was hydrogenated in the presence of 2 g of 10% palladium/charcoal for 4 hours at 40° C. under 5 bar of hydrogen pressure. The crude product obtained after conventional working up was purified by column chromatography over silica gel (30-60 μm) using FM1/cyclohexane 9/1 (v/v) as eluant. Colourless crystals, Rf=0.3 (FM1/cyclohexane 9/1 (v/v)); Macherey-Nagel POLYGRAM® SIL G/UV254, ready-made films for TLC). Yield: 1.7 g (40.7% of theory).

Sources & evidence

ORD record
ord-d5eced98e88047eaa4bbdc008c01c5b9
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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