Diphenylphosphinic chloride → HCID 18914232, compound

HRID 1292110Notes

Reaction equation

HRID 1292110 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[CH2:18][CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:37]([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)[CH:38]([CH3:40])[CH3:39]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([N:44]2[CH2:45][CH2:46][N:41]([CH2:37][CH:38]([CH3:40])[CH3:39])[CH2:42][CH2:43]2)=[O:15])=[CH:11][C:10]=1[CH2:18][CH:19]([CH3:21])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 73910Diphenylphosphinic chlorideHCID 20520521-(2-Methylpropyl)piperazineHCID 15462893HCID 15462893, compound

Product 1

HCID 18914232HCID 18914232, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

4-benzyloxy-3-isobutylbenzoic acid (4.94 g) was dissolved in a mixture of chloroform (60 ml) and triethylamine (4.83 ml). To this mixture, diphenylphosphinic chloride (3.66 ml) was added while being cooled with ice. After being stirred for 40 minutes, the mixture, with 1-isobutylpiperazine (2.48 g) added thereto, was stirred for 1.5 hours at room temperature. The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine successively, dried over sodium sulfate anhydride, and then concentrated under a vacuum. Thus obtained residue was purified by silica gel column chromatography (chloroform: methanol=50:1), thereby yielding 7.11 g of the aimed compound.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 1.5 hours at room temperature
  3. washThe reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum
  6. customThus obtained residue was purified by silica gel column chromatography (chloroform: methanol=50:1)

Sources & evidence

ORD record
ord-c57c853afcea4443b47d83ebee9d3f13
Source dataset
uspto-grants-1998_05
Patent number
US05756505

Reaction notes

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