Diphenylphosphinic chloride → HCID 69942011, compound

HRID 1637602Notes

Reaction equation

HRID 1637602 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:15]([OH:17])=O)/[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.[NH2:38][CH2:39][CH:40]1[CH2:44][CH2:43][CH2:42][N:41]1[CH2:45][CH3:46]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:45]([N:41]1[CH2:42][CH2:43][CH2:44][CH:40]1[CH2:39][NH:38][C:15](=[O:17])[C:14]1[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:12]([O:11][CH2:1]/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4])[CH:13]=1)[CH3:46]

Participants

6

Reactant 3

HCID 73910Diphenylphosphinic chlorideHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 25066810HCID 25066810, compound

Product 1

HCID 69942011HCID 69942011, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

3-geranyloxy-4-methoxybenzoic acid(1.52 g) was dissolved in chloroform (50 ml) and triethylamine (1.4 ml), and then diphenylphosphinic chloride(1.0 ml) was added thereto while being cooled with ice. After being stirred for 15 minutes, the mixture, with 2-aminomethyl-1-ethylpyrrolidine(0.7 ml) added thereto, was stirred for 1.5 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), thereby yielding 1.47 g(71%) 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 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)

Sources & evidence

ORD record
ord-411b8e67040c4a7a99d5e3dd5ed15931
Source dataset
uspto-grants-2000_03
Patent number
US06043243

Reaction notes

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