Phthalimide → N-{1-(6-Chloropyridin-2-yl)-2-(pyridin-2-yl)ethyl}phthalimide

HRID 1736481Notes

Reaction equation

HRID 1736481 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8](O)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:36]1(=[O:46])[NH:40][C:39](=[O:41])[C:38]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([N:40]2[C:39](=[O:41])[C:38]3=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]3[C:36]2=[O:46])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 541195581-(6-Chloropyridin-2-yl)-2-(pyridin-2-yl)ethyl alcohol

Product 1

HCID 19973564N-{1-(6-Chloropyridin-2-yl)-2-(pyridin-2-yl)ethyl}phthalimideYield 128.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

38.6 g of the 1-(6-chloropyridin-2-yl)-2-(pyridin-2-yl)ethyl alcohol prepared in the Preparative Example 20, 47.8 g of triphenylphosphine and 26.8 g of phthalimide were dissolved in 500 ml of tetrahydrofuran, followed by the addition thereto of 31.7 g of diethyl azodicarboxylate. The obtained mixture was stirred at room temperature overnight and concentrated, followed by the addition thereto of diethyl ether. The obtained mixture was filtered to remove insolubles and the filtrate was purified by silica gel chromatography (with a hexane/ethyl acetate (2:1) mixture) to give 77.1 g of the title compound as a roughly purified product.

Workup

  1. additionfollowed by the addition
  2. concentrationconcentrated
  3. additionfollowed by the addition
  4. filtrationThe obtained mixture was filtered
  5. customto remove insolubles
  6. customthe filtrate was purified by silica gel chromatography (with a hexane/ethyl acetate (2:1) mixture)

Sources & evidence

ORD record
ord-61ee13c25f52433eb2d245d18a7869a2
Source dataset
uspto-grants-1996_07
Patent number
US05541213

Reaction notes

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