Potassium Carbonate → HCID 11329788, compound

HRID 1831768Notes

Reaction equation

HRID 1831768 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:21]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1>CN(C=O)C>[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)[CH2:25][CH2:24]2)=[O:22])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 131725190HCID 131725190, compound

Product 1

HCID 11329788HCID 11329788, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.050 g (0.112 mmol) of {3-[2-(2,4-Dichlorophenyl)-ethoxy]-4-methoxy-phenyl}-piperazin-1-yl-methanone, hydrochloride salt was dissolved in 3 ml of DMF. 61.9 mg (0.448 mmol) of potassium carbonate was added to the solution, followed by 0.021 g (0.11 mmol) of 1-Bromomethyl-4-fluoro-benzene. The reaction solution was shaken for 16 h at RT. The solvent was removed under reduced pressure, the residue was taken-up in ethyl acetate and the solution was washed twice with water and once with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with n-heptane/ethyl acetate (1/1), and DCM/MeOH (10/1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe solution was washed twice with water and once with saturated aqueous sodium chloride
  3. dry with materialThe organic phase was dried with magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with n-heptane/ethyl acetate (1/1), and DCM/MeOH (10/1)

Sources & evidence

ORD record
ord-11b69016337141e4a1b51550596d7df3
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

Loading…