Hydrochloric Acid → (3S)-3-methyl-1-{[2-methyl-5-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 43382Notes

Reaction equation

HRID 43382 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([S:8]([C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:12]=2[CH3:21])(=[O:10])=[O:9])[CH2:5][CH2:4][N:3]1C(OC(C)(C)C)=O.Cl>O1CCOCC1>[CH3:1][C@@H:2]1[NH:3][CH2:4][CH2:5][N:6]([S:8]([C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:18])[F:19])[CH:14]=[CH:13][C:12]=2[CH3:21])(=[O:9])=[O:10])[CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666496631,1-dimethylethyl(2S)-2-methyl-4-{[2-methyl-5-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinecarboxylate

Product 1

HCID 66649648(3S)-3-methyl-1-{[2-methyl-5-(trifluoromethyl)phenyl]sulfonyl}piperazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1,1-dimethylethyl (2S)-2-methyl-4-{[2-methyl-5-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinecarboxylate (may be prepared as described in Description 26) (2.1 g, 4.97 mmol) in 1,4-Dioxane (50 mL) was treated by 4 M HCl in dioxane (6.21 mL, 24.85 mmol). The reaction mixture was stirred overnight at room temperature. LCMS showed a 1:1 ratio between starting material and expected product. 4 M HCl in dioxane (6.21 mL, 24.85 mmol) was added and the reaction mixture stirred for 4 h. LCMS showed about 10% of remaining starting material. 4 M HCl in dioxane (6.21 mL, 24.85 mmol) was added and the reaction mixture stirred for 1 h.

Sources & evidence

ORD record
ord-25964f6d868d4613b5348bdd85ac8a33
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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