Hydrochloric Acid → (Methylsulfonyl)(2-Piperazinylphenyl)Amine

HRID 228070Notes

Reaction equation

HRID 228070 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][N:15](CC2C=CC=CC=2)[CH2:14][CH2:13]1)(=[O:4])=[O:3].CO.Cl>[Pd].CCOC(C)=O>[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21935090N-[2-(4-Benzylpiperazin-1-yl)phenyl]methanesulfonamide

Product 1

HCID 19261360(Methylsulfonyl)(2-Piperazinylphenyl)Amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a round-bottomed flask equipped with stirring was added (methylsulfonyl){2-[4-benzylpiperazinyl]phenyl}amine (42 g, 120 mmol), MeOH, 10% Pd/C (Aldrich) (25 g), and HCO2NH4 (38 g, 610 mmol) After heating at reflux for 2 h, the mixture was filtered through Celite® and washed with CH2Cl2. The combined organic layers were washed with NaHCO3 and concentrated in vacuo to afford a light yellow solid. This was treated with a soln of EtOAc and HCl to afford the salt of the desired compound as the hydrochloride salt (20 g). MS (ESI, pos. Ion) m/z: 256 (M+H); MS (ESI, neg. Ion) m/z: 254 (M−H). Calc'd for C11H17N3O2S: 255.10.

Workup

  1. customTo a round-bottomed flask equipped
  2. temperatureAfter heating
  3. temperatureat reflux for 2 h
  4. filtrationthe mixture was filtered through Celite®
  5. washwashed with CH2Cl2
  6. washThe combined organic layers were washed with NaHCO3
  7. concentrationconcentrated in vacuo
  8. customto afford a light yellow solid

Sources & evidence

ORD record
ord-0083a9e0c54e4748bba7837658adbeb3
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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