Hydrochloric Acid → 3-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile

HRID 2365444Notes

Reaction equation

HRID 2365444 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[C@@H:14]([CH3:25])[CH2:13]2)(=[O:11])=[O:10])=[C:5]([CH3:26])[CH:4]=1)#[N:2].Cl.O1CCOCC1>C(Cl)Cl>[CH3:26][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[S:9]([N:12]1[CH2:17][CH2:16][NH:15][C@@H:14]([CH3:25])[CH2:13]1)(=[O:11])=[O:10])[C:1]#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 591520981,1-dimethylethyl(2S)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate2×

Product 1

HCID 591520673-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrileYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl (2S)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate (may be prepared as described in Intermediate 12; 5.52 g, 14.54 mmol) was dissolved in DCM (80 ml) and then 4M hydrochloric acid in dioxane (36.3 mL, 145 mmol) was added at room temperature and the reaction mixture was stirred for two hours. The solvent was removed under vacuum to give the title compound (4.0 g) as a white solid.

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-3f4b335022074763b446ec998d081525
Source dataset
uspto-grants-2014_04
Patent number
US08697703B2

Reaction notes

Loading…