Water → (2R*,4S*)-2-benzyl-1-(2-naphthoyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

HRID 264612

Reaktionsgleichung

Reaktionsgleichung von HRID 264612
S(Cl)(Cl)=O.[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[C:15]([OH:17])=O.[CH2:18]([C@@H:25]1[CH2:30][C@@H:29]([N:31]([CH2:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[N:42]=[CH:41][CH:40]=2)[C:32](=[O:37])[C:33]([F:36])([F:35])[F:34])[CH2:28][CH2:27][NH:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:18]([C@@H:25]1[CH2:30][C@@H:29]([N:31]([CH2:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[N:42]=[CH:41][CH:40]=2)[C:32](=[O:37])[C:33]([F:35])([F:36])[F:34])[CH2:28][CH2:27][N:26]1[C:15]([C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=1)=[O:17])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 71232-Naphthoic acidHCID 24386Thionyl ChlorideHCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Produkt 1

HCID 57190025(2R*,4S*)-2-benzyl-1-(2-naphthoyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 58 μl (0.795 mmol) of thionyl chloride in 0.2 ml of toluene is added dropwise to a solution of 97 mg (0.56 mmol) of 2-naphthoic acid in 1 ml of toluene over the course of 10 minutes at 50° under argon, and the reaction mixture is stirred at 80° for 2 hours. It is then concentrated in a rotary evaporator, and 1 ml of toluene is added, and evaporation is repeated, twice each. The brown oil is dissolved in 1 ml of methylene chloride and added under argon to a solution of 200 mg (0.468 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine at 0° and stirred at 0° for 2 hours. Water is subsequently added to the reaction mixture, and extraction with methylene chloride is carried out. The organic phases are washed with brine, dried over magnesium sulfate and evaporated to dryness. The yellow oil is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (1000:50:1). The title compound is obtained as yellow oil. TLC: methylene chloride/methanol/conc. ammonia (2000:50:1) Rf =0.36, FD-MS: M+ =581.

Aufarbeitung

  1. concentrationIt is then concentrated in a rotary evaporator, and 1 ml of toluene
  2. additionis added
  3. customevaporation
  4. dissolutionThe brown oil is dissolved in 1 ml of methylene chloride
  5. stirringstirred at 0° for 2 hours
  6. washThe organic phases are washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness
  9. customThe yellow oil is chromatographed on silica gel with methylene chloride/methanol/conc

Quellen und Nachweise

ORD-Eintrag
ord-ac2157718c5f4f1a9ec01bc60d904c53
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646144

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