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Sodium Hydroxide → HCID 59455232, Verbindung

HRID 1401623
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1401623
[CH3:1][N:2]1[CH2:30][CH2:29][C:5]2[N:6]([CH2:14][C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)O)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.S(Cl)(Cl)=O.[OH-].[Na+]>C(Cl)Cl.CN(C=O)C>[C:23]1([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]3[CH2:3][N:2]([CH3:1])[CH2:30][CH2:29][C:5]2=3)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 59454957HCID 59454957, Verbindung

Produkt 1

HCID 59455232HCID 59455232, VerbindungAusbeute 15,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of 2-(2,8-Dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1,1-diphenyl-ethanol (100 mg, 0.25 mmol) in DCM (5 mL) and DMF (2 drops) was stirred at 0-10° C. Thionyl chloride (1.55 mL, 21.46 mmol) was added and the reaction mixture was stirred at RT for 2.5 h. The solvent was removed under vacuum to obtain crude yellow solid. 1N NaOH (10 mL) was added to the reaction mixture and the desired compound extracted with EtOAc (20 mL×2). The organic layer was dried over anhydrous sodium sulfate, concentrated under vacuum to obtain the crude product (90 mg) which was purified by column chromatography on silica gel (100-200 mesh) using eluent 0-3% MeOH and DCM to obtain 15 mg product which was converted to HCL salt. 1H NMR (CD3OD, HCl salt) δ (ppm): 7.40 (m, 5H), 7.22-7.16 (m, 6H), 6.98 (m, 3H), 4.62 (d, 1H), 4.30 (m, 1H), 3.62 (m, 1H), 3.36 (m, 1H), 2.98 (s, 3H), 2.80 (m, 2H), 2.40 (s, 3H).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customto obtain crude yellow solid
  3. extractionthe desired compound extracted with EtOAc (20 mL×2)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto obtain the crude product (90 mg) which
  7. customwas purified by column chromatography on silica gel (100-200 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-e094e4a9a3044e6e846112e29b2e11ff
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08907097B2

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