Trifluoroacetic acid → 5-Chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[perhydro-azepine-3,3'-piperidine]

HRID 2068501

Reaktionsgleichung

Reaktionsgleichung von HRID 2068501
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:17][CH2:16][CH2:15]/[C:14](=[CH:18]/OC)/[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[ClH:21].ClC1C=C[C:26]([NH:29]N)=CC=1.F[C:32](F)(F)[C:33](O)=O.C([SiH](CC)CC)C.[OH-].[NH4+]>C(Cl)(Cl)Cl.ClCCl>[Cl:21][CH:33]1[CH2:32][CH2:26][NH:29][CH2:13][C:14]2([CH2:15][CH2:16][CH2:17][N:11]([CH2:10]/[CH:9]=[CH:8]/[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12]2)[CH2:18]1

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14923Ammonium HydroxideHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 68924237[(e)-3-(4-Chloro-phenyl)-allyl]-4-[1-methoxy-meth-(z)-ylidene]-perhydro-azepine

Produkt 1

HCID 689278545-Chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[perhydro-azepine-3,3'-piperidine]

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of -[(E)-3-(4-Chloro-phenyl)-allyl]-4-[1-methoxy-meth-(Z)-ylidene]-perhydro-azepine (0.6 g) and 4-chlorophenylhydrazine hydrochloride (0.41 g) in chloroform (20 ml) was treated with trifluoroacetic acid (2.1 ml) and heated at reflux under argon for 18 hours. The reaction mixture was cooled to room temperature, triethylsilane (3.1 ml) was added and the solution refluxed for 2 hours. The reaction mixture was cooled to room temperature, diluted with dichloromethane, neutralised with 30% aqueous ammonium hydroxide, washed with brine, dried (sodium sulphate) and concentrated. The dark residue was purified by silica gel chromatography (cyclohexane:ethyl acetate 1:9) to afford 5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[perhydro-azepine-3,3′-piperidine] (529 mg). MS (ES+) 387/389 (M+H+).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux under argon for 18 hours
  3. temperaturethe solution refluxed for 2 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. washwashed with brine
  6. dry with materialdried (sodium sulphate)
  7. concentrationconcentrated
  8. customThe dark residue was purified by silica gel chromatography (cyclohexane:ethyl acetate 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-330aff8920e54441bb4e7d6b9fe25fb1
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299058B2

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