Diisopropylethylamine → 1,1-dimethylethyl(2S)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate

HRID 2365443Notes

Reaction equation

HRID 2365443 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].CCN(C(C)C)C(C)C.[C:24]([C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[C:28]([CH3:36])[CH:27]=1)#[N:25]>C(Cl)Cl>[C:24]([C:26]1[CH:31]=[CH:30][C:29]([S:32]([N:6]2[CH2:5][CH2:4][N:3]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[C@@H:2]([CH3:1])[CH2:7]2)(=[O:34])=[O:33])=[C:28]([CH3:36])[CH:27]=1)#[N:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylateHCID 545947681251110-16-3

Product 1

HCID 591520981,1-dimethylethyl(2S)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylateYield 104.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (2.79 g, 13.91 mmol, supplier Antlantic Scitech) in DCM (80 mL), DIPEA (3.64 mL, 20.87 mmol) was added under argon atmosphere at room temperature then 4-cyano-2-methylbenzenesulfonyl chloride (3 g, 13.91 mmol) was added at 0° C. The ice bath was removed and the reaction mixture was stirred overnight. The reaction mixture was partitioned between DCM (30 ml) and aqueous sodium bicarbonate (2×20 ml). The organic phase was washed with HCl (2×20 ml) and water (2×20 ml) then it was dried (phase separator) and concentrated under vacuum to give the title compound (5.5 g) as a yellow viscous liquid.

Workup

  1. customThe ice bath was removed
  2. customThe reaction mixture was partitioned between DCM (30 ml) and aqueous sodium bicarbonate (2×20 ml)
  3. washThe organic phase was washed with HCl (2×20 ml) and water (2×20 ml)
  4. customit was dried (phase separator)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-40483658d8bd4ead9776bf6f2bc44866
Source dataset
uspto-grants-2014_04
Patent number
US08697703B2

Reaction notes

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