Ammonium Chloride → HCID 46743507, compound

HRID 2365439Notes

Reaction equation

HRID 2365439 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[C:26]([CH3:34])[CH:25]=1.[NH4+].[Cl-]>C(Cl)Cl>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)(=[O:32])=[O:31])=[C:26]([CH3:34])[CH:25]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27813384-Bromo-2-methylbenzenesulfonyl chloride

Product 1

HCID 46743507HCID 46743507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 1-piperazinecarboxylate (1.86 g, 9.99 mmol, supplier Aldrich) and DIPEA (2.62 ml, 14.98 mmol) in dry DCM (20 ml) at 0° C. under argon was added 4-bromo-2-methylbenzenesulfonyl chloride (2.96 g, 10.99 mmol) and the resulting yellow solution allowed to warm to rt, then stirred at rt for 18 h. Semi-saturated NH4Cl (40 ml) was added, then the aq extracted with DCM (30 ml). The combined organics were passed through a hydrophobic frit, then concentrated in vacuo to give the title compound as a yellow gum that became a solid on standing (4.72 g).

Workup

  1. extractionthe aq extracted with DCM (30 ml)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e066f466d3bf403cb1cec954ea25c49c
Source dataset
uspto-grants-2014_04
Patent number
US08697703B2

Reaction notes

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