Pyridine → N1-(4-methoxybenzoyl)-N2-[1-(tert-butoxycarbonyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine

HRID 395695

Reaktionsgleichung

Reaktionsgleichung von HRID 395695
[C:1](Cl)(Cl)=[O:2].[C:5]([O:9][C:10](N1CCC(CO)CC1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[CH3:20][O:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([NH:28][C:29]2[C:30]([NH2:35])=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:27])=[CH:24][CH:23]=1.[N:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[O:44]1CCC[CH2:45]1>C1(C)C=CC=CC=1.C(Cl)Cl.C(OCC)(=O)C.O>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH:28][C:29]2[C:30]([NH:35][C:45]([O:2][CH:1]([CH:41]3[CH2:42][CH2:43][NH:38][CH2:39][CH2:40]3)[C:10]([O:9][C:5]([CH3:6])([CH3:7])[CH3:8])=[O:11])=[O:44])=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:27])=[CH:36][CH:37]=1

Komponenten

10

Edukt 5

HCID 1049PyridineHCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 785232N-(2-Aminophenyl)-4-methoxybenzamideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Produkt 1

HCID 86585753N1-(4-methoxybenzoyl)-N2-[1-(tert-butoxycarbonyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1.9 M phosgene in toluene (2.0 mL) was treated with 1-(tert-butoxycarbonyl)-4-hydroxymethylpiperidine (200 mg, 0.930 mmol). After 1 h, the mixture was concentrated in vacuo and the residue dried under high vacuum for 4 h. The residue was dissolved in methylene chloride (2.5 mL) and then added dropwise to a solution of N1-(4-methoxybenzoyl)-1,2-benzenediamine (230 mg, 0.950 mmol) and pyridine (0.4 mL) in methylene chloride (5 mL) and tetrahydrofuran (1 mL). After 16 h, the mixture was poured into a mixture of water and ethyl acetate. The organic layer was washed once with 1.0 N aqueous hydrochloric acid, once with saturated sodium chloride solution, dried (potassium carbonate), and filtered. Concentration and purification of the residue by flash chromatography (silica gel, ethyl acetate/hexanes) yielded 416 mg (93%) of the title compound.

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue dried under high vacuum for 4 h
  3. dissolutionThe residue was dissolved in methylene chloride (2.5 mL)
  4. waitAfter 16 h
  5. washThe organic layer was washed once with 1.0 N aqueous hydrochloric acid, once with saturated sodium chloride solution
  6. dry with materialdried (potassium carbonate)
  7. filtrationfiltered
  8. concentrationConcentration and purification of the residue by flash chromatography (silica gel, ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0754f222815940268f72032513eeb72b
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605626B2

Verknüpfte Notizen

Wird geladen…