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Triphenylphosphine → 6-(3-Piperidin-1-yl-propoxy)-quinoline-2-carboxylic acid ethyl ester

HRID 493427
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 493427
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:36]1([CH2:42][CH2:43][CH2:44]O)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C1(C)C=CC=CC=1.C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:44][CH2:43][CH2:42][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:12]=2)[N:7]=1)=[O:5])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 66032Piperidine-1-propanolHCID 57681568Ethyl 6-hydroxyquinoline-2-carboxylate

Produkt 1

HCID 576815716-(3-Piperidin-1-yl-propoxy)-quinoline-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

A mixture of 0.400 g (0.002 mol) of 6-hydroxy-quinoline-2-carboxylic acid ethyl ester, 0.966 g (0.004 mmol) of triphenylphospine (Fluka), 0.396 g (0.003 mmol) of 3-piperidin-1-yl-propan-1-ol and 0.68 ml (0.004 mmol) of di-tert.-butyl azadicarboxylate 40% in toluene in 40 ml THF was stirred for a prolonged period of time at 35° C. The mixture was filtered through a pad of silica and washed with 30 ml THF. The mixture was evaporated to dryness and purified on silica eluting with a gradient of DCM/MeOH/NH4OH from 97/3/0.5 to 90/10/0.5. The product fractions were evaporated and the residue was triturated with diethyl ether to yield after drying under vacuum 0.600 g (93%) of the title compound as white solid. MS (m/e): 343.3 (M+H)+.

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of silica
  2. washwashed with 30 ml THF
  3. customThe mixture was evaporated to dryness
  4. custompurified on silica eluting with a gradient of DCM/MeOH/NH4OH from 97/3/0.5 to 90/10/0.5
  5. customThe product fractions were evaporated
  6. customthe residue was triturated with diethyl ether
  7. customto yield
  8. dry with materialafter drying under vacuum 0.600 g (93%) of the title compound as white solid

Quellen und Nachweise

ORD-Eintrag
ord-b00283c4652847368c5c1aa4a71f9cdd
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07534891B2

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