1-Methylpiperazine → (1R, 2R)-2-[(4-methylpiperazin-1-yl)carbonyl]-1-cyclohexanecarboxylic acid

HRID 413723Notes

Reaction equation

HRID 413723 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C@@H:8]12[C:17](=[O:18])[O:16][C:14](=[O:15])[C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13]2>O1CCOCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:17]([C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]2[C:14]([OH:16])=[O:15])=[O:18])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 12261141(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride

Product 1

HCID 751551(1R, 2R)-2-[(4-methylpiperazin-1-yl)carbonyl]-1-cyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

0.37 cm3 of N-methylpiperazine in solution in 5 cm3 of dioxane is added, under an argon atmosphere, to 0.50 g of (−)-trans-1,2-cyclohexanedicarboxylic anhydride in solution at −15° C. in 20 cm3 of dioxane. After 1.25 hours at 20° C., the reaction mixture is filtered, the solid is washed with 20 cm3 of diethyl ether, drained, and then dried under reduced pressure (2,7 kPa) at 20° C., to give 0.65 g of (1R, 2R)-2-[(4-methylpiperazin-1-yl)carbonyl]-1-cyclohexanecarboxylic acid in the form of a white solid.

Workup

  1. filtrationthe reaction mixture is filtered
  2. washthe solid is washed with 20 cm3 of diethyl ether
  3. customdried under reduced pressure (2,7 kPa) at 20° C.

Sources & evidence

ORD record
ord-35bf9627e9d84c20b7872f2fec1e7667
Source dataset
uspto-grants-2003_05
Patent number
US06569854B1

Reaction notes

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