Ethanol → HCID 178460675, compound

HRID 48937Notes

Reaction equation

HRID 48937 reaction equation
[N:1]1([CH2:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.ClC[P:19](C)(C)=[O:20].[C:23](=O)([O-])[O-].[K+].[K+].[CH2:29](O)[CH3:30]>[Cl-].[Na+].O>[CH3:23][C:29]([CH3:30])([PH2:19]=[O:20])[N:4]1[CH2:5][CH2:6][N:1]([CH2:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 74224Phosphine oxide, (chloromethyl)dimethyl-HCID 176060554-(1-Piperazinylmethyl)benzoic acid

Product 1

HCID 178460675HCID 178460675, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-Piperazin-1-ylmethyl-benzoic acid (4c) and chloro-(dimethyl-phosphinoyl)-methane (5a) in ethanol was added potassium carbonate. The resulting reaction mixture was refluxed, then cooled to room temperature, diluted with brine, acidified to pH-4, and extracted with EtOAc until the aqueous layer showed little or no evidence of product by HPLC. The combined organics were dried over MgSO4 and concentrated on rotary evaporator. The desired product was purified by silica gel flash chromatography.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed
  3. extractionextracted with EtOAc until the aqueous layer
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated on rotary evaporator
  6. customThe desired product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-ede405ec21084346b6e3a0daa2d97f5b
Source dataset
uspto-grants-2004_03
Patent number
US06706699B2

Reaction notes

Loading…