1-Methylpiperazine → HCID 86607093, compound

HRID 2108874Notes

Reaction equation

HRID 2108874 reaction equation
[Br:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>O1CCCC1>[BrH:1].[OH:10][C:6]1[C:7](=[O:9])[CH:8]=[C:3]([CH2:2][N:15]2[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]2)[O:4][CH:5]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 10976603KOJIC ACID, 2-BROMOMETHYL ANALOG

Product 1

HCID 86607093HCID 86607093, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

2-(Bromomethyl)-5-hydroxy-4H-pyran-4-one 21 (0.5 g, 2.4 mmol), 1-methylpiperazine (0.3 mL, 2.4 mmol) and tetrahydrofurane (12 mL) were charged in a 250 ml round-bottomed flask equipped with a magnetic stirrer. The reaction mixture was stirred for 2 h at 75° C. The reaction mixture was cooled and the precipitate was filtered to give after drying 5-hydroxy-2-((4-methylpiperazin-1-yl)methyl)-4H-pyran-4-one hydrobromide 23 (0.6 g, 83% yield) as a beige solid. A cesium salt was prepared by adding to Cs2CO3 (7.3 g, 22.4 mmol) in water (20 mL). The aqueous phase was washed with CH2Cl2 (200 mL), then water was evaporated at 40° C. and the cesium salt was drying under vacuum to give a white powder.

Workup

  1. customequipped with a magnetic stirrer
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe precipitate was filtered
  4. customto give

Sources & evidence

ORD record
ord-151ff86453d94af2b49bd62468456ec6
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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