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Triethylamine → Ethyl 5-{[2-(2-{[3-chloro-4'-(trifluoromethyl)biphenyl-4-yl]methoxy}-phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

HRID 875325
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 875325
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)[CH:7]=[CH:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][NH:20][CH:21]1[CH2:30][CH2:29][CH2:28][C:27]2[N:26]=[C:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:24]=[CH:23][C:22]1=2.C(N(CC)CC)C>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([C:36]2[CH:37]=[CH:38][C:39]([C:42]([F:45])([F:43])[F:44])=[CH:40][CH:41]=2)[CH:7]=[CH:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][NH:20][CH:21]1[CH2:30][CH2:29][CH2:28][C:27]2[N:26]=[C:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:24]=[CH:23][C:22]1=2
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Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 86709814Ethyl 5-{[2-(2-{[3-chloro-4'-(trifluoromethyl)biphenyl-4-yl]methoxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride

Produkt 1

HCID 86709815Ethyl 5-{[2-(2-{[3-chloro-4'-(trifluoromethyl)biphenyl-4-yl]methoxy}-phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

78 g (111.39 mmol) of ethyl 5-{[2-(2-{[3-chloro-4′-(trifluoromethyl)biphenyl-4-yl]methoxy}-phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride (Enantiomer 2, Example 80A) were taken up in 1200 ml of THF, 47 ml of triethylamine were added and the mixture was stirred at room temperature for 1 h. The precipitated triethylammonium chloride crystals were then filtered off and washed with THF. The filtrate obtained was evaporated to dryness. The residue was dissolved in ethyl acetate, washed twice with 10% strength aqueous sodium chloride solution, dried over magnesium sulphate, filtered and once more evaporated to dryness. This gave 69 g (111.24 mmol, 99.9% of theory) of the target compound.

Aufarbeitung

  1. filtrationThe precipitated triethylammonium chloride crystals were then filtered off
  2. washwashed with THF
  3. customThe filtrate obtained
  4. customwas evaporated to dryness
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed twice with 10% strength aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customonce more evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-feff3ecc65234576873585f7f9301469
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08981104B2

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