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Sodium Hydroxide → HCID 178464530, Verbindung

HRID 1269816
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1269816
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C@H:11]3[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=O)[CH3:19])[CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[ClH:29].C(OCC)C>O1CCCC1.O>[ClH:29].[CH2:18]([NH:17][C@H:14]1[CH2:13][CH2:12][C@H:11]([O:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[CH2:16][CH2:15]1)[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 10953452Ether hydrochlorideHCID 21226445Aluminium lithium hydrideHCID 178475035HCID 178475035, Verbindung

Produkt 1

HCID 178464530HCID 178464530, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
2×
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The trans-N-[4-(1H-indazol-5-yloxy)cyclohexyl]acetamide (0.066 g, 0.24 mmol) obtained in Example 391 was added to a suspension of lithium aluminum hydride (0.040 g, 1.05 mmol) in tetrahydrofuran (5 ml) and stirred for 12 hours with heating under reflux. The resulting solution was cooled on an ice bath, followed by adding dropwise thereto water (0.05 ml), a 2N-aqueous sodium hydroxide solution (0.10 ml) and water (0.15 ml) in that order. Thereafter, the insoluble material was removed by filtration using Celite. The filtrate was purified by a silica gel chromatography (eluent: chloroform/methanol/30%-aqueous ammonia=10/1/0 to 100/10/1). A solution of the purified material in ethyl acetate was prepared and a 1N-hydrochloric acid/diethyl ether solution (0.5 ml) was added thereto. The solid precipitated was subjected to decantation with ethyl acetate and dried up to obtain trans-N-ethyl-4-(1H-indazol-5-yloxy)cyclohexanamine monohydrochloride (0.057 g, 80%).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperatureThe resulting solution was cooled on an ice bath
  4. additionby adding dropwise
  5. customThereafter, the insoluble material was removed by filtration
  6. customThe filtrate was purified by a silica gel chromatography (eluent: chloroform/methanol/30%-aqueous ammonia=10/1/0 to 100/10/1)
  7. customA solution of the purified material in ethyl acetate was prepared
  8. customThe solid precipitated
  9. customdried up

Quellen und Nachweise

ORD-Eintrag
ord-c438213fd5224db980a62bbdbc874f47
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07199147B2

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