Water → Tert-butyl 4-(2-chloro-5-nitrophenylsulfonyl)piperazine-1-carboxylate

HRID 244363Notes

Reaction equation

HRID 244363 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CCOC(C)=O.O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([N:18]1[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]1)(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 206302-Chloro-5-nitrobenzenesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 59260816Tert-butyl 4-(2-chloro-5-nitrophenylsulfonyl)piperazine-1-carboxylateYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 37 (0.600 g, 2.34 mmol) in DCM (20.00 mL) was added tert-butyl 1-piperazinecarboxylate (0.566 g, 3.04 mmol) and TEA (0.422 mL, 3.04 mmol). The reaction was monitored with TLC (25% EtOAc in hexanes, Rf=0.53). The reaction mixture was complete after stirring at room temperature for 1 hr, as indicated by the absence of the starting material (TLC). Water was added and aqueous layer was extracted twice with DCM. Combined extracts were sequentially washed with water and brine, dried over MgSO4, filtered, and evaporated in vacuo to afford a yellow solid. The solid was triturated with DCM and hexanes, and then filtered to yield compound 38 as a yellow solid (0.789 g, 100% HPLC purity, 83% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.60 (d, J=3 Hz, 1H), 8.47 (dd, J1=3 Hz, J2=8 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 3.37 (m, 4H), 3.23 (m, 4H), 1.37 (s, 9H).

Workup

  1. extractionaqueous layer was extracted twice with DCM
  2. washCombined extracts were sequentially washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a yellow solid
  7. customThe solid was triturated with DCM and hexanes
  8. filtrationfiltered

Sources & evidence

ORD record
ord-078429561bef4952be1dfa8c2e9147db
Source dataset
uspto-grants-2014_02
Patent number
US08658642B2

Reaction notes

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