Triphenylphosphine → HCID 86749664, compound

HRID 1736410Notes

Reaction equation

HRID 1736410 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:13][NH:14][CH2:15][CH2:16][CH2:17][OH:18])[O:10]2)=[CH:5][CH:4]=1.O[C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1.CO.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:13][NH:14][CH2:15][CH2:16][CH2:17][O:18][C:25]3[CH:26]=[N:27][C:28]4[C:23]([CH:24]=3)=[CH:22][CH:21]=[CH:20][CH:29]=4)[O:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10514903HCID 10514903, compoundHCID 1354268667-Hydroxyquinoline

Product 1

HCID 86749664HCID 86749664, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 3-(7-methoxy-chroman-2-ylmethyl-amino)-propanol (3.07 g, 13 mmol), 7-hydroxy quinoline (1.88 g, 13 mmol), triphenylphosphine (3.67 g, 14 mmol) in anhydrous tetrahydrofuran (50 mL) was slowly added a solution of diethylazodicarboxylate (2.44 g, 14 mmol) in tetrahydrofuran (10 ml). The reaction was allowed to stir for 3 hours and was then quenched with water, extracted with methylene chloride (150 mL) dried over anhydrous magnesium sulfate, filtered and the solvent removed under vacuum. Chromatography (2.5% MeOH -methylene chloride) afforded 2.72 g of the title compound (55% yield) which was converted to the monohydrate, dimaleate salt in tetrahydrofuran, mp 132°-134° C.

Workup

  1. customwas then quenched with water
  2. extractionextracted with methylene chloride (150 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-2c966512f84e4df18934b5660d4e2243
Source dataset
uspto-grants-1996_07
Patent number
US05541199

Reaction notes

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