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Trifluoroacetic acid → N-[1-(4-Methoxybenzyl)-piperidin-3-ylmethyl]-N-phenyl-propionamide

HRID 479789
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 479789
FC(F)(F)C(O)=O.[C:8]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][N:22]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:23](=[O:26])[CH2:24][CH3:25])[CH2:16]1)(OC(C)(C)C)=O.C(=O)[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:41][O:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:8][N:15]2[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][N:22]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:23](=[O:26])[CH2:24][CH3:25])[CH2:16]2)=[CH:35][CH:36]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 312444-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 12991578N-(1-Boc-piperidin-3-ylmethyl)-N-phenyl-propionamide

Produkt 1

HCID 12108346N-[1-(4-Methoxybenzyl)-piperidin-3-ylmethyl]-N-phenyl-propionamideAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (0.5 mL) was added dropwise to a solution of N-(1-Boc-piperidin-3-ylmethyl)-N-phenyl-propionamide 5 (31 mg, 0.090 mmol) in 0.5 mL of dry CH2Cl2 at 0° C. (ice-water). The reaction mixture was stirred at room temperature for 30 minutes. TLC showed the reaction was complete. After removal of the solvents, the residue was dried under vacuum for 3 hrs. The crude compound was dissolved in DMF (0.5 mL) and 4-anisaldehyde (16.7 μL, 1.5 eq.) was added. The mixture was stirred at room temperature for 30 min. NaB(OAc)3H (95%, 28.45 mg, 1.5 eq.) was introduced in one portion, and the mixture was shaken at room temperature overnight. The mixture was quenched with 5 mL of aqueous potassium carbonate (sat.), then extracted with ethyl acetate (3×10 mL). The extracts were combined and washed with aqueous NaHCO3 (sat., 2×5 mL), brine (10 mL), and dried over anhydrous sodium sulfate. After the solvent was removed, the remaining oily residue was purified by preparative thin layer chromatography (EtOAc/MeOH, 9:1) to afford N-[1-(4-Methoxybenzyl)-piperidin-3-ylmethyl]-N-phenyl-propionamide 10 as a colorless oil (18.7 mg, 59%). LRMS 366.

Aufarbeitung

  1. customAfter removal of the solvents
  2. customthe residue was dried under vacuum for 3 hrs
  3. dissolutionThe crude compound was dissolved in DMF (0.5 mL)
  4. stirringThe mixture was stirred at room temperature for 30 min
  5. stirringthe mixture was shaken at room temperature overnight
  6. customThe mixture was quenched with 5 mL of aqueous potassium carbonate (sat.)
  7. extractionextracted with ethyl acetate (3×10 mL)
  8. washwashed with aqueous NaHCO3 (sat., 2×5 mL), brine (10 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customAfter the solvent was removed
  11. customthe remaining oily residue was purified by preparative thin layer chromatography (EtOAc/MeOH, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-8219851ac6f44148b493bb2d6a0ecc75
Quelldatensatz
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06645980B1

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