Water → HCID 23130993, compound

HRID 493694Notes

Reaction equation

HRID 493694 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[H-].[Na+].[Cl:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([S:28][CH2:29][CH2:30][CH2:31]Cl)[CH:24]=2)[CH:19]=1.O>CN(C=O)C>[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([S:28][CH2:29][CH2:30][CH2:31][N:7]1[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3][C:2]1=[O:1])[CH:22]=[CH:21]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 68834688HCID 68834688, compound

Product 1

HCID 23130993HCID 23130993, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 3-oxopiperazine-1-carboxylate (2.0 g) was dissolved in DMF (30 mL), and sodium hydride (0.5 g) was added thereto. With ice cooling, 2-chloro-6-((3-chloropropyl)thio)naphthalene (2.7 g) was added thereto, and the mixture was mixed at 60° C. for 3 hours. The reaction solution was poured into water, then extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified with a silica gel column to give the title compound (4.0 g) as a pale brown oily matter.

Workup

  1. additionthe mixture was mixed at 60° C. for 3 hours
  2. extractionextracted with chloroform
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified with a silica gel column

Sources & evidence

ORD record
ord-3d3cdaaff79741aa9bf162a574b552a9
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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