Water → (S)-N-(2,3-dihydro-7H-1,4-dioxino[2,3-e]indazol-2-ylmethyl)-1-[1-(2-methoxyphenyl)piperid-4-yl]methylamine

HRID 1532054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1532054
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH2:22])[CH2:17][CH2:16]1.[OH2:23].C[N:25]([CH3:28])C=O>C1(C)C=CC=CC=1>[O:4]1[C:1]2=[C:9]3[C:28](=[CH:13][CH:12]=[C:11]2[O:23][CH2:16][C@@H:17]1[CH2:18][NH:22][CH2:21][CH:18]1[CH2:19][CH2:20][N:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH3:7])[CH2:16][CH2:17]1)[NH:25][N:15]=[CH:10]3

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10608971(1-(2-Methoxyphenyl)piperidin-4-yl)methanamine

Produkt 1

HCID 22951194(S)-N-(2,3-dihydro-7H-1,4-dioxino[2,3-e]indazol-2-ylmethyl)-1-[1-(2-methoxyphenyl)piperid-4-yl]methylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of the product from the previous reaction (0.25 g), potassium carbonate (2 g) and 1-[1-(2-methoxyphenyl)piperid-4-yl]methylamine (0.3 g) in a mixture of dimethylformamide (5 ml) and toluene (10 ml) was heated at reflux temperature for 8 hours. The cooled mixture was poured into water (100 ml) and extracted with ethyl ether (2×100 ml). The combined extracts were then dried over magnesium sulphate and the solvent removed under reduced pressure to yield a yellow oil. Purification by flash column chromatography on silica eluting with a 20:1 mixture of dichloromethane and methanol afforded (S)-N-(2,3-dihydro-7H-1,4-dioxino[2,3-e]indazol-2-ylmethyl)-1-[1-(2-methoxyphenyl)piperid-4-yl]methylamine (0.04 g) as a gummy solid.

Aufarbeitung

  1. additionA mixture of the product
  2. temperaturewas heated
  3. temperatureat reflux temperature for 8 hours
  4. extractionextracted with ethyl ether (2×100 ml)
  5. dry with materialThe combined extracts were then dried over magnesium sulphate
  6. customthe solvent removed under reduced pressure
  7. customto yield a yellow oil
  8. customPurification by flash column chromatography on silica eluting
  9. additionwith a 20:1 mixture of dichloromethane and methanol

Quellen und Nachweise

ORD-Eintrag
ord-d592b71b7cb345bb8cdfb1addac17b7b
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06201004B1

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