Acetic Acid → (3,5-Bis-trifluoromethyl-benzyl)-[2-(4-cyclohexylmethyl-piperazin-1-yl)-quinolin-3-ylmethyl]-amine

HRID 1911746

Reaktionsgleichung

Reaktionsgleichung von HRID 1911746
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6][NH2:7].[CH:17]1([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]3[C:39]([CH:40]=O)=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH2:26][CH2:25]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:12])[F:13])[CH:10]=1)[CH2:6][NH:7][CH2:40][C:39]1[C:30]([N:27]2[CH2:26][CH2:25][N:24]([CH2:23][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:29][CH2:28]2)=[N:31][C:32]2[C:37]([CH:38]=1)=[CH:36][CH:35]=[CH:34][CH:33]=2

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 574868172-[4-(Cyclohexylmethyl)piperazin-1-yl]quinoline-3-carbaldehyde

Produkt 1

HCID 57486818(3,5-Bis-trifluoromethyl-benzyl)-[2-(4-cyclohexylmethyl-piperazin-1-yl)-quinolin-3-ylmethyl]-amineAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3,5-Bis(trifluoromethyl) benzylamine (0.305 g, 1.25 mmol) was added to a solution of 2-(4-cyclohexylmethyl-piperazin-1-yl)-quinoline-3-carbaldehyde (0.4 g, 1.23 mmol) in methanol followed by acetic acid (0.15 mL) at ambient temperature under nitrogen atmosphere. After stirring 1 h, sodium cyanoborohydride (0.237 g, 3.77 mmol) was added carefully, and the reaction was stirred at RT for overnight. The reaction mixture was evaporated to dryness, and water (30 mL) and ethyl acetate (30 mL) were added to the residue, and this was then extracted with ethyl acetate (2×30 mL). The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated under vacuum to afford a pale yellow crude product. Purification by silica gel column chromatography and eluting with 2.5% methanol/dichloromethane afforded the title compound (0.468 g, yield: 67%).

Aufarbeitung

  1. stirringthe reaction was stirred at RT for overnight
  2. customThe reaction mixture was evaporated to dryness, and water (30 mL) and ethyl acetate (30 mL)
  3. additionwere added to the residue
  4. extractionthis was then extracted with ethyl acetate (2×30 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto afford a pale yellow crude product
  10. customPurification by silica gel column chromatography
  11. washeluting with 2.5% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-497702a547354a319a6bf21e58a40ded
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604055B2

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