Laurolactam → n-(cis-2-Phenyl-cyclopentyl) azacyclotridecan-2-imine-hydrochloride

HRID 1704213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1704213
[C:1]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2]1.P(Cl)(Cl)([Cl:17])=O.Cl.[C:21]1([C@H:27]2[CH2:31][CH2:30][CH2:29][C@H:28]2[NH2:32])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1C=CC=CC=1>[ClH:17].[C:21]1([C@H:27]2[CH2:31][CH2:30][CH2:29][C@H:28]2[N:32]=[C:1]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 13690LaurolactamHCID 24813Phosphorus oxychlorideHCID 70051154rac-(1R,2R)-2-phenylcyclopentan-1-amine hydrochloride

Produkt 1

HCID 136349517n-(cis-2-Phenyl-cyclopentyl) azacyclotridecan-2-imine-hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To 21.7 g of 2-azacyclotridecanone in 200 ml of dry benzene was added dropwise 15.3 g of phosphorus oxychloride. The mixture was stirred at room temperature for 4 hours after which 19.8 g of cis-2-phenylcyclopentylamine hydrochloride was added. The reaction mixture was stirred at room temperature for 2 hours and refluxed for 24 hours. The resulting homogeneous solution was washed with 2N NaOH, 2N HCl and saturated NaCl solution, dried over sodium sulfate and the solvent evaporated. The resulting oily product crystallized from acetone and was recrystallized from methanol-acetone to give the desired product, M.P. 156°-159° C.

Aufarbeitung

  1. additionwas added
  2. temperaturerefluxed for 24 hours
  3. washThe resulting homogeneous solution was washed with 2N NaOH, 2N HCl and saturated NaCl solution
  4. dry with materialdried over sodium sulfate
  5. customthe solvent evaporated
  6. customThe resulting oily product crystallized from acetone
  7. customwas recrystallized from methanol-acetone

Quellen und Nachweise

ORD-Eintrag
ord-23f8cdbdb9b44cf4b24aad1522099911
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04126611

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