4-Chlorobenzenesulfonyl chloride → 1,1-Dimethylethyl (3S)-4-[(4-chlorophenyl)sulfonyl]-3-methyl-1-piperazinecarboxylate

HRID 43365Notes

Reaction equation

HRID 43365 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:7]2[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][C@@H:2]2[CH3:1])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 7023035(S)-1-Boc-3-methylpiperazine

Product 1

HCID 582844531,1-Dimethylethyl (3S)-4-[(4-chlorophenyl)sulfonyl]-3-methyl-1-piperazinecarboxylateYield 129%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1,1-dimethylethyl (3S)-3-methyl-1-piperazinecarboxylate (10.0 g, 49.9 mmol, supplier Aldrich) in pyridine (30 ml) was added 4-chlorobenzenesulfonyl chloride (12.7 g, 59.9 mmol) portionwise. The reaction was stirred at room temperature under an argon atmosphere for 2 hours. The reaction was then evaporated, partitioned between 2N aq. HCl (70 ml) and DCM (80 ml). The aqueous was further extracted with DCM (2×80 ml) and the combined DCM layers were passed through a hydrophobic frit and evaporated. The product was dried under vacuum at 40° C. for 18 hours to yield the title compound as an orange solid (24.14 g).

Workup

  1. customThe reaction was then evaporated
  2. custompartitioned between 2N aq. HCl (70 ml) and DCM (80 ml)
  3. extractionThe aqueous was further extracted with DCM (2×80 ml)
  4. customevaporated
  5. customThe product was dried under vacuum at 40° C. for 18 hours

Sources & evidence

ORD record
ord-062b751f57374ed49721c0a60226a5e8
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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