Acetic Acid → N-phenyl-N-((2R)-2-piperazinylmethyl)methanesulfonamide

HRID 1972616Notes

Reaction equation

HRID 1972616 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][C@@H:9]1[CH2:21][N:22]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[S:23]([CH3:26])(=[O:25])=[O:24])C1C=CC=CC=1.CC(O)=O.CCO>[Pd].CCOC(C)=O>[C:27]1([N:22]([CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)[S:23]([CH3:26])(=[O:25])=[O:24])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 66582506N-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-N-phenylmethanesulfonamide

Product 1

HCID 66582514N-phenyl-N-((2R)-2-piperazinylmethyl)methanesulfonamideYield 119.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 150-mL round-bottomed flask was charged with N-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-N-phenylmethanesulfonamide (0.527 g, 1.172 mmol, step 2), AcOH (0.10 mL, 1.7 mmol), Pd (10 wt. % (dry basis) on activated carbon, wet, Degussa type, 0.528 g), EtOH (10 mL) and EtOAc (2 mL). The reaction mixture was evacuated under vacuum and refilled with hydrogen. The mixture was stirred under an atmosphere of hydrogen at room temperature for 4.5 h then at 50° C. for 12 h. The reaction mixture was filtered and the filtrate was concentrated and re-subjected to the reaction condition (Pd/C 0.683 g and EtOH 10 mL). The reaction mixture was evacuated under vacuum and refilled with hydrogen. The mixture was stirred under an atmosphere of hydrogen at 50° C. for 12 h. The reaction mixture was filtered through a pad of filter agent. The filtrate was concentrated to give N-phenyl-N-((2R)-2-piperazinylmethyl)methanesulfonamide (0.378 g) as a clear oil.

Workup

  1. customThe reaction mixture was evacuated under vacuum
  2. additionrefilled with hydrogen
  3. waitat 50° C. for 12 h
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe reaction mixture was evacuated under vacuum
  7. additionrefilled with hydrogen
  8. stirringThe mixture was stirred under an atmosphere of hydrogen at 50° C. for 12 h
  9. filtrationThe reaction mixture was filtered through a pad of filter agent
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0285e32ab2764789b2467f2979aef31b
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

Loading…