Potassium Carbonate → 4-[4-(Diethoxy-phosphorylmethyl)-piperazin-1-ylmethyl]-benzoic acid

HRID 50632Notes

Reaction equation

HRID 50632 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.[CH2:17]([O:19][P:20]([CH2:25]Cl)(=[O:24])[O:21][CH2:22][CH3:23])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(O)C.[Cl-].[Na+].O>[CH2:17]([O:19][P:20]([CH2:25][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)([O:21][CH2:22][CH3:23])=[O:24])[CH3:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 76633Phosphonic acid, P-(chloromethyl)-, diethyl esterHCID 176060554-(1-Piperazinylmethyl)benzoic acid

Product 1

HCID 206345494-[4-(Diethoxy-phosphorylmethyl)-piperazin-1-ylmethyl]-benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-Piperazin-1-ylmethyl-benzoic acid (4c) and chloromethyl-phosphonic acid diethyl ester (4d) 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-67e25cb957584aa59a373f9e477579a2
Source dataset
uspto-grants-2004_03
Patent number
US06713462B2

Reaction notes

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