Diphenylphosphinic chloride → HCID 9888723, compound

HRID 1292113Notes

Reaction equation

HRID 1292113 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=2[CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:4][CH:3]=1.C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:38]([N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)[CH:39]([CH3:41])[CH3:40]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([N:45]3[CH2:46][CH2:47][N:42]([CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:43][CH2:44]3)=[O:14])=[CH:10][C:9]=2[CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 73910Diphenylphosphinic chlorideHCID 20520521-(2-Methylpropyl)piperazineHCID 15383033HCID 15383033, compound

Product 1

HCID 9888723HCID 9888723, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

4-(4-fluorobenzyloxy)-3-isobutylbenzoic acid (16.5 g) was dissolved in a mixture of chloroform (150 ml) and triethylamine (15.3 ml). To this mixture was added diphenylphosphinic chloride (11.5 ml) while being cooled with ice. After being stirred for 40 minutes, the mixture, with 1-isobutylpiperazine (7.83 g) added thereto, was stirred for 1.5 hours at room temperature. This reaction mixture was washed with saturated 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) and the resulting solid was recrystallized (from n-hexane), thereby yielding 19.6 g of the aimed compound.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 1.5 hours at room temperature
  3. washThis reaction mixture was washed with saturated 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)
  7. customthe resulting solid was recrystallized (from n-hexane)

Sources & evidence

ORD record
ord-ab3dc70d69c44d0794bfdded32fb0c7e
Source dataset
uspto-grants-1998_05
Patent number
US05756505

Reaction notes

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