Dimethylformamide → 6-Phenylazepan-2-one

HRID 569752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 569752
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.CN1CCOCC1.CN(C)C=O.Cl.[NH2:31][CH2:32][CH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:34][CH2:35][CH2:36][C:37](O)=[O:38]>C(OCC)(=O)C.O>[C:40]1([CH:33]2[CH2:32][NH:31][C:37](=[O:38])[CH2:36][CH2:35][CH2:34]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 199401P,P-Diphenylphosphinic azideHCID 679105716-Amino-5-phenylhexanoic acid hydrochloride

Produkt 1

HCID 127649286-Phenylazepan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

27.6 ml of diphenylphosphoryl azide and then 37.5 ml of N-methylmorpholine were added to 260 ml of dimethylformamide containing 26.0 g of 6-amino-5-phenylhexanoic acid hydrochloride [prepared as described in step (c) above] in an ice-bath. The reaction mixture was stirred for 3.5 hours at room temperature, and then dissolved in 0.5 liter of ethyl acetate and 0.5 liter of water. The ethyl acetate layer was separated, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was subjected to silica gel column chromatography using a 2:1 by volume mixture of ethyl acetate and methylene chloride as eluent, to give 4.0 g of the title compound as crystals, melting at 153.5°-154.5° C. (with decomposition).

Aufarbeitung

  1. customThe ethyl acetate layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. additionby volume mixture of ethyl acetate and methylene chloride as eluent

Quellen und Nachweise

ORD-Eintrag
ord-1c7deeb93ff3471b9d9fd5f051853c33
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04734410

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