Chlorosuccinimide → HCID 66870162, compound

HRID 1971231Notes

Reaction equation

HRID 1971231 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-494f68b8c8d1476c89ec91a2a653b637
Source dataset
uspto-grants-2013_04
Patent number
US08431592B2

Reaction notes

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