Triethylamine → 1-(4-benzyl-piperazin-1-yl)-(S)-2-(4-pentyl-benzylamino)-3-phenyl-propan-1-one

HRID 563132

Reaktionsgleichung

Reaktionsgleichung von HRID 563132
Cl.[CH2:2]([C@H:9]([N:25]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[CH:43][CH:42]=1)C(=O)C=CC1C=CC(C(F)(F)F)=CC=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.C(C1C=CC(C=O)=CC=1)CCCC.[BH4-].[Na+]>CO.O>[CH2:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10](=[O:11])[C@@H:9]([NH:25][CH2:40][C:41]2[CH:42]=[CH:43][C:44]([CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[CH:45][CH:46]=2)[CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:17][CH2:16]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 23290Benzaldehyde, 4-pentyl-HCID 4311764Sodium borohydrideHCID 67005149N-[(S)-1-Benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(4-pentyl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide hydrochloride

Produkt 1

HCID 598082551-(4-benzyl-piperazin-1-yl)-(S)-2-(4-pentyl-benzylamino)-3-phenyl-propan-1-oneAusbeute 33,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

N—[(S)-1-Benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(4-pentyl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide hydrochloride (2 g, 5.55 mmol) was dissolved in methanol (50 mL), followed by the addition of triethylamine (0.562 g, 5.55 mmol) and 4-n-pentylbenzaldehyde (1.076 g, 6.10 mmol). The mixture was heated to reflux for 5 h, cooled to rt and sodium borohydride (0.6 g, 15.8 mmol) was added in several portions over a period of 60 min. Stirring at rt was continued for 12 h, followed by the addition of water (2 mL). The mixture was concentrated under reduced pressure, to the residue was added water (100 mL) and the product was extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (silicagel, heptane/EtOAc=1/1) to give 906 mg (32%) of 1-(4-benzyl-piperazin-1-yl)-(S)-2-(4-pentyl-benzylamino)-3-phenyl-propan-1-one. LC-MS: tR=0.77 min; [M+H]+=484.44.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 h
  3. concentrationThe mixture was concentrated under reduced pressure, to the residue
  4. additionwas added water (100 mL)
  5. extractionthe product was extracted with EtOAc (3×100 mL)
  6. washThe combined organic layers were washed with brine (100 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by column chromatography (silicagel, heptane/EtOAc=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-431a715e64ad4747ab2609d86b1a8df4
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067419B2

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