4-Chlorophenol → 4-(4-Chlorophenoxy)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-piperidine hydrochloride

HRID 745330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 745330
[F:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]3)=[N:7][O:8][C:4]=2[CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1>[ClH:21].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([O:18][CH:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][CH2:9][C:6]3[C:5]4[CH:19]=[CH:20][C:2]([F:1])=[CH:3][C:4]=4[O:8][N:7]=3)[CH2:17][CH2:16]2)=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 133198661-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxypiperidine

Produkt 1

HCID 133198684-(4-Chlorophenoxy)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-piperidine hydrochlorideAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

To a solution of 9.5 g of 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxypiperidine, 4.5 g of 4-chlorophenol and 9.8 g triphenylphosphine in 250 ml of benzene, cooled with an ice-bath, was slowly added over one hour a solution of 6.4 g of diethyl azodicarboxylate in 60 ml of benzene. After stirring one hr at ambient temperature, the reaction mixture was filtered and then concentrated to an oil. The oil was treated with ethereal hydrogen chloride to give 4.6 g (32%) of product, mp 209°-211° C. Recrystallization from ethyl acetate/methanol gave the analytical sample, mp 212°-213° C. (dec).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated to an oil
  3. additionThe oil was treated with ethereal hydrogen chloride

Quellen und Nachweise

ORD-Eintrag
ord-f13ed5a16c24423da1092442970af257
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04598152

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