Diisopropylethylamine → 4-(4-Nitro-2-trifluoromethyl-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl ester

HRID 1841944Notes

Reaction equation

HRID 1841944 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[N+:26]([C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=1)([O-:28])=[O:27]>C(Cl)Cl>[CH2:10]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([S:35]([C:32]2[CH:33]=[CH:34][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][C:31]=2[C:39]([F:40])([F:41])[F:42])(=[O:37])=[O:36])[CH2:22][CH2:21]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 643495Benzyl piperazine-1-carboxylateHCID 108034044-Nitro-2-(trifluoromethyl)benzene-1-sulfonyl chloride

Product 1

HCID 569547274-(4-Nitro-2-trifluoromethyl-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (1.2 ml, 7.0 mmol) was added in one portion to a stirred solution of piperazine-1-carboxylic acid benzyl ester (0.76 g, 3.5 mmol) in DCM (15 ml) at room temperature. To this mixture was added 4-nitro-2-trifluoromethyl-benzenesulfonyl chloride (1.0 g, 3.5 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time, the mixture was diluted with DCM (20 ml), washed with HCl (1M, 20 ml) and NaOH (1M, 20 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum to give the title compound (1.43 g, 87% yield) as a purple solid. δH (500 MHz, DMSO) 8.65-8.60 (2H, m), 8.31 (1H, d), 7.38-7.29 (5H, m), 5.07 (2H, s), 3.56-3.46 (4H, m), 3.30-3.25 (4H, m). Tr=2.25 min m/z (ES+) (M+Na+) 496.

Workup

  1. washwashed with HCl (1M, 20 ml) and NaOH (1M, 20 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e729fecb220d49feb5654f5133847de6
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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