1-Methylpiperazine → 4-Methylpiperazine-1-carboxamide

HRID 626544Notes

Reaction equation

HRID 626544 reaction equation
[C:1](=[O:10])(OC1C=CC=CC=1)[NH2:2].[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>CC#N.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:1]([NH2:2])=[O:10])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 69322Phenyl carbamate

Product 1

HCID 4102614-Methylpiperazine-1-carboxamideYield 68%

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of phenyl carbamate (20.0 g, 146 mmol) in MeCN (200 mL) was added N-methylpiperazine (20.00 g, 200 mmol) followed by catalytic amount of ytterbium triflate (0.500 g, 1.061 mmol) and the resulting mixture was heated at 80° C. for 1 h. The solvent from the reaction mixture was completely evaporated and the residue was crystallized from MTBE to provide 4-methylpiperazine-1-carboxamide (14.2 g, 68% yield) as white solid 1H NMR (400 MHz, DMSO-d6): δ 5.92 (s, 2H), 3.42 (t, J=4.9 Hz, 4H), 2.19 (t, J=4.9 Hz, 4H), 2.14 (s, 3H).

Workup

  1. customThe solvent from the reaction mixture was completely evaporated
  2. customthe residue was crystallized from MTBE

Sources & evidence

ORD record
ord-595f204a14c54ab191ade6c88de3a1b8
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

Loading…