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Diisopropylethylamine → 2-(4-(4-Fluoro-benzoyl)-piperidin-1-ylmethyl]-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-one

HRID 362247
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 362247
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:25][C:16]3=[C:17]4[C:21](=[CH:22][CH:23]=[C:15]3[O:14][CH2:13]2)[NH:20][C:19](=[O:24])[CH2:18]4)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:38][C:39]1[CH:52]=[CH:51][C:42]([C:43]([CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)=[O:44])=[CH:41][CH:40]=1.C(N(C(C)C)CC)(C)C.CCCCCC.C(OCC)(=O)C>CS(C)=O>[F:38][C:39]1[CH:40]=[CH:41][C:42]([C:43]([CH:45]2[CH2:50][CH2:49][N:48]([CH2:11][CH:12]3[O:25][C:16]4=[C:17]5[C:21](=[CH:22][CH:23]=[C:15]4[O:14][CH2:13]3)[NH:20][C:19](=[O:24])[CH2:18]5)[CH2:47][CH2:46]2)=[O:44])=[CH:51][CH:52]=1
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Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 15381104(R)-2-(Toluene-4-sulfonyloxymethyl)-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-oneHCID 21226206Ethyl acetate hexaneHCID 73011315(4-Fluorophenyl)(piperidin-4-yl)methanone 4-methylbenzenesulfonate

Produkt 1

HCID 543705752-(4-(4-Fluoro-benzoyl)-piperidin-1-ylmethyl]-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-one
Ausbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

(R)-2-(Toluene-4-sulfonyloxymethyl)-2,3,8,9-tetrahydro-7H- 1,4-dioxino[2,3-e]indol-8-one (1.03 g, 2.75 mmole), 4-(4-fluorobenzoyl)piperidine p-toluenesulfonate (4.68 g, 12.4 mmole) and diisopropylethylamine (2.15 ml, 12.3 mmole) were combined in 70 ml of dry DMSO and heated to 85° C. for 5 hours under a nitrogen atmosphere. The reaction was cooled and taken into 400 ml of 1:1 hexane/ethyl acetate. This was washed with 200 ml of water, with 200 ml of saturated brine, dried over MgSO4, filtered and concentrated to yield an oil. This oil was column chromatographed on silica gel using 0.75% methanol/CH2Cl2 as eluant to give the free base of the title compound as a yellow oil (0.40 g, 40%). This oil was crystallized from ethanol with the addition of a solution of fumaric acid in hot ethanol to give 0.37 g of the (S) enantiomer of the title compound as a light yellow solid fumarate, m.p. 237°-238° C.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. washThis was washed with 200 ml of water, with 200 ml of saturated brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield an oil
  7. customchromatographed on silica gel using 0.75% methanol/CH2Cl2 as eluant

Quellen und Nachweise

ORD-Eintrag
ord-99ec1f92caa641a883d67e164a3c2b92
Quelldatensatz
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05869490

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