Chlorosuccinimide → HCID 66870162, compound

HRID 1670484Notes

Reaction equation

HRID 1670484 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-36734baedd14452e97df651059c9b4b1
Source dataset
uspto-grants-2011_08
Patent number
US07994170B2

Reaction notes

Loading…