1-(2,3-Xylyl)piperazine → HCID 69605101, compound

HRID 860004Notes

Reaction equation

HRID 860004 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.BrC1C=CC(S(O[CH2:26][C@@H:27]2[O:41][C:31]3=[C:32]4[C:37](=[CH:38][CH:39]=[C:30]3[O:29][CH2:28]2)[N:36]=[C:35]([CH3:40])[CH:34]=[CH:33]4)(=O)=O)=CC=1>CS(C)=O.C(=O)(O)[O-].[Na+]>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:26][C@@H:27]2[O:41][C:31]3=[C:32]4[C:37](=[CH:38][CH:39]=[C:30]3[O:29][CH2:28]2)[N:36]=[C:35]([CH3:40])[CH:34]=[CH:33]4)[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 705411-(2,3-Xylyl)piperazineHCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate

Product 1

HCID 69605101HCID 69605101, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(2,3-dimethylphenyl)-piperazine (1.13 g, 5.94 mmol) and [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzene-sulfonate (871 mg, 1.93 mmol) in anhydrous DMSO (10 mL) was heated overnight at 70° C. The reaction was diluted with saturated aqueous sodium bicarbonate (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography on silica gel (50% EtOAc/hexanes) afforded 700 mg (90%) of the title compound as a white solid: mp 112–113° C.; MS (ESI) m/z 404 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dfef642342e24d8d81e6c217653f1eaf
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

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