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Diphenylphosphinic chloride → 3-[2-(4-Geranyloxybenzoylamino)ethylamino]pyridine

HRID 850404
Notes
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Reaction equation

HRID 850404 reaction equation
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:36][CH2:37][CH2:38][NH:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:36][CH2:37][CH2:38][NH:39][C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)=[O:18])=[CH:19][CH:20]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 73910Diphenylphosphinic chlorideHCID 123615004-Geranyloxybenzoic acidHCID 14834213N-pyridin-3-ylethane-1,2-diamine

Product 1

HCID 154342383-[2-(4-Geranyloxybenzoylamino)ethylamino]pyridineYield 47.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent
HCID 8471
Triethylamine
Solvent

Procedure

4-geranyloxybenzoic acid(3.57 g) was dissolved in chloroform(60 ml) and triethylamine(3.60 ml), and then diphenylphosphinic chloride(2.48 ml) was added thereto while being cooled with ice. After being stirred for 30 minutes, the mixture, with 3-(2-aminoethylamino)pyridine(2.24 g) added thereto, was stirred for 3 hours at room temperature. The reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=15:1). The resulting solid was recrystallized from n-hexane/ethyl acetate, thereby yielding 2.41 g of the aimed compound.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 3 hours at room temperature
  3. washThe reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=15:1)
  7. customThe resulting solid was recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-f90557e5dfe54d1e893bda4a73f7bf62
Source dataset
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06017937

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes