Triphenylphosphine → 4-(6-Morpholin-4-ylhexyl)-salicylamide

HRID 644788

Reaktionsgleichung

Reaktionsgleichung von HRID 644788
[CH:1]1[CH:2]=[CH:3][C:4]2[O:12]C(=O)[NH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.O[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH-].[Na+]>O1CCCC1>[N:20]1([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:2]2[CH:3]=[C:4]([OH:12])[C:5](=[CH:6][CH:1]=2)[C:7]([NH2:9])=[O:8])[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1

Komponenten

7

Edukt 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 162582H-1,3-Benzoxazine-2,4(3H)-dioneHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 222185044-Morpholinehexanol

Produkt 1

HCID 670704014-(6-Morpholin-4-ylhexyl)-salicylamideAusbeute 37,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A slurry of carsalam (6.13 g, 37.6 mmol), 4-(6-hydroxyhexyl)morpholine (7.0 g, 37.4 mmol), triphenylphosphine (9.97 g, 35.0 mmol), and tetrahydrofuran (40 mL) was treated with a solution of diisopropyl azodicarboxylate (7.40 mL, 7.60 g, 37.6 mmol) and tetrahydrofuran (10 mL), added dropwise over 15 minutes. The reaction mixture was stirred at 25° C. for 60 hours. The solution was treated with aqueous 2N NaOH (50 mL, 100 mmol) and warmed to 60° C. for 180 minutes. The cooled reaction mixture was concentrated to remove the tetrahydrofuran. The aqueous residue was washed with ethyl acetate (2×40 mL), and was acidified with 4% aqueous HCl to a pH of 0.84 (causing carbon dioxide gas to evolve). The pH of the aqueous phase was raised to 7.8 with 2N aqueous NaOH. Solid sodium bicarbonate was added. Extraction with ethyl acetate (8×40 mL), drying over sodium sulfate and concentration gave an oil which solidified upon standing. A total of 4.26 g of 4-(6-morpholin-4-ylhexyl)-salicylamide was isolated.

Aufarbeitung

  1. additionadded dropwise over 15 minutes
  2. temperaturewarmed to 60° C. for 180 minutes
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated
  5. customto remove the tetrahydrofuran
  6. washThe aqueous residue was washed with ethyl acetate (2×40 mL)
  7. temperatureThe pH of the aqueous phase was raised to 7.8 with 2N aqueous NaOH
  8. additionSolid sodium bicarbonate was added
  9. extractionExtraction with ethyl acetate (8×40 mL)
  10. dry with materialdrying over sodium sulfate and concentration
  11. customgave an oil which

Quellen und Nachweise

ORD-Eintrag
ord-4410d9785cd14ba78083bb38ac16f57d
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700775B2

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