Hydrochloric Acid → 4-(3-Benzylpyrrolidin-1-yl)-2-methyl-6-phenoxyquinoline hydrochloride

HRID 408660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408660
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=2)[N:5]=[C:4]([CH3:19])[CH:3]=1.[CH2:20]([CH:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>C(OCCO)C.[OH-].[Na+]>[ClH:1].[CH2:20]([CH:27]1[CH2:31][CH2:30][N:29]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:10]=3)[N:5]=[C:4]([CH3:19])[CH:3]=2)[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 38297913-BenzylpyrrolidineHCID 167672894-Chloro-2-methyl-6-phenoxyquinoline

Produkt 1

HCID 687777994-(3-Benzylpyrrolidin-1-yl)-2-methyl-6-phenoxyquinoline hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8076Glycol monoethyl etherLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

4-Chloro-2-methyl-6-phenoxyquinoline (0.2 g; see Preparation 3 above) and 3-benzyl-pyrrolidine (0.3 g) in 2-ethoxyethanol (4 mL) were heated in a microwave to 200° C. for 20 minutes. The mixture was diluted with 1 N sodium hydroxide and extracted with ethyl acetate, dried (MgSO4), filtered and evaporated. The residue was purified by preparative HPLC, the relevant fractions combined and evaporated to give a clear oil which was acidified with concentrated hydrochloric acid and then evaporated. Trituration with ether gave the title compound as a white powder.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by preparative HPLC
  6. customevaporated
  7. customto give a clear oil which
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-76dbcac6c7f54639a52933205e94a590
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759348B2

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