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Thionyl Chloride → 3-Benzo[1,3]dioxol-5-ylpiperidin-1-yl-(R)-2,3-dihydrobenzo[1,4]dioxin-2-ylmethanone

HRID 2365968
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2365968
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11]([OH:13])=O.S(Cl)(Cl)=O.Cl.[O:19]1[C:23]2[CH:24]=[CH:25][C:26]([CH:28]3[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]3)=[CH:27][C:22]=2[O:21][CH2:20]1.CCN(C(C)C)C(C)C>C(Cl)Cl.O.C1(C)C=CC=CC=1>[O:19]1[C:23]2[CH:24]=[CH:25][C:26]([CH:28]3[CH2:33][CH2:32][CH2:31][N:30]([C:11]([C@@H:2]4[O:1][C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=5[O:4][CH2:3]4)=[O:13])[CH2:29]3)=[CH:27][C:22]=2[O:21][CH2:20]1
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Komponenten

8

Edukt 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 687062(R)-1,4-Benzodioxane-2-carboxylic acidHCID 667274853-benzo[1,3]dioxol-5-yl-piperidine HCl

Produkt 1

HCID 667272583-Benzo[1,3]dioxol-5-ylpiperidin-1-yl-(R)-2,3-dihydrobenzo[1,4]dioxin-2-ylmethanoneAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of (R)-2,3-dihydrobenzo[1,4]dioxine-2-carboxylic acid (167 mg, 0.93 mmol), thionyl chloride (338 μl, 551 mg, 4.63 mmol) and dry toluene was heated at 95° C. for 1.5 h and then evaporated to dryness. Toluene was added and the evaporation was repeated. The evaporation residue was dissolved in DCM (2 ml) and added slowly to a cold solution (0° C.) of 3-benzo[1,3]dioxol-5-yl-piperidine HCl (224 mg, 0.93 mmol) and DIPEA (0.324 ml, 240 mg, 1.85 mmol) in DCM (5 ml). The reaction mixture was stirred for 1 h 45 min at RT. Water was added, layers were separated and the organic phase was washed twice with 1 M HCl and sat. NaHCO3. The organic phase was dried (Na2SO4), filtered and evaporated to give 290 mg of the title compound.

Aufarbeitung

  1. customevaporated to dryness
  2. additionToluene was added
  3. customthe evaporation
  4. dissolutionThe evaporation residue was dissolved in DCM (2 ml)
  5. customlayers were separated
  6. washthe organic phase was washed twice with 1 M HCl and sat. NaHCO3
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cee0d6bfafa740eeb322a8cc30f415ed
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08697723B2

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