1-Hydroxybenzotriazole → 2,3-Dihydro-1-benzoxepine-4-carboxamide

HRID 565947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 565947
N1(C2C=CC([C:13]3[CH:14]=[CH:15][C:16]4[O:22][CH2:21][CH2:20][C:19]([C:23](O)=[O:24])=[CH:18][C:17]=4[CH:26]=3)=CC=2)CCCCC1.C[N:28](CC1C=CC(N)=CC=1)C1CCOCC1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[O:22]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:26][C:17]=2[CH:18]=[C:19]([C:23]([NH2:28])=[O:24])[CH2:20][CH2:21]1

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 184722357-(4-Piperidinophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid

Produkt 1

HCID 184723002,3-Dihydro-1-benzoxepine-4-carboxamideAusbeute 221,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 7-(4-piperidinophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (0.15g), 4-(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)aniline (0.1g) and 1hydroxy-benzotriazole (0.07g) in dimethylformamide (10ml) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.13g) under ice-cooling. Under nitrogen atmosphere, the mixture was warmed to room temperature. To the mixture were added 4-dimethylaminopyridine (catalytic amount) and triethylamine (0.18ml), and the mixture was stirred over night. The solvent was evaporated, and to the residue was added water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 7-(4-piperidinophenyl)-N-(4-((N-methyl-N-tetrahydro-pyran-4-yl)amino)-methyl)-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 151) (0.18g) as colorless crystals.

Aufarbeitung

  1. temperaturecooling
  2. customThe solvent was evaporated
  3. additionto the residue was added water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated
  8. customto give crude crystals, which
  9. customwere recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-5a6dd8317d9e42a58aee36a4e5307869
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172061B2

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