7-Chloro-benzo[1,4]dioxin-2-one → 2-(4-Chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

HRID 11615Notes

Reaction equation

HRID 11615 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[O:7][C:6]=2[CH:12]=1.[F:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][N:19]2[CH2:24][C@H:23]([CH3:25])[NH:22][CH2:21][C@H:20]2[CH3:26])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:9][C:8]([N:22]2[CH2:21][C@H:20]([CH3:26])[N:19]([CH2:18][C:17]3[CH:27]=[CH:28][C:14]([F:13])=[CH:15][CH:16]=3)[CH2:24][C@H:23]2[CH3:25])=[O:11])=[C:6]([OH:7])[CH:12]=1

Participants

4

Reactant 2

HCID 32553187-Chloro-benzo[1,4]dioxin-2-oneHCID 23405839(2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine

Product 1

HCID 537887242-(4-Chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanoneYield 63.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 7-chloro-benzo[1,4]dioxin-2-one (0.48 g, 2.6 mmol) in toluene (5 mL) was added 1-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazine (0.59 g, 2.6 mmol). The resulting mixture was heated to 95° C. overnight. The reaction was cooled to ambient temperature and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.67 g).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fa15cbc844647a681a1b88e23376cc0
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

Loading…