Chlorosuccinimide → HCID 66870162, compound

HRID 1446123Notes

Reaction equation

HRID 1446123 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:23]N1C(=O)CCC1=O>C(O)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)[CH2:10][CH:9]1[Cl:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 33806961-Boc-4-(4-Nitrophenyl)piperazine

Product 1

HCID 66870162HCID 66870162, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1.25 g (4 mmol) of 4-(4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (Example 75c) in 10 ml of isopropanol are added 0.72 g (4.2 mmol) of N-chlorosuccinimide. The solution is stirred for 6 h at 50° C. After this time, the solution is evaporated to dryness and the residue is dissolved in 100 ml of EtOAc. The solution is extracted with water, dried over MgSO4 and evaporated to dryness to provide the title compound: ES-MS: 342.2, 344.2 (M+H)+; analytical HPLC: tret=5.70 minutes (Grad 2).

Workup

  1. customAfter this time, the solution is evaporated to dryness
  2. dissolutionthe residue is dissolved in 100 ml of EtOAc
  3. extractionThe solution is extracted with water
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-cb579cc69b8c4c5f80fa38e2d72b7afd
Source dataset
uspto-grants-2010_02
Patent number
US07667039B2

Reaction notes

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