Water → N-[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(4-pentyl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide

HRID 563133

Reaktionsgleichung

Reaktionsgleichung von HRID 563133
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)=[CH:5][CH:4]=1.[CH2:16]([N:23]1[CH2:28][CH2:27][N:26]([C:29](=[O:51])[C@@H:30]([NH:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:42][CH:41]=2)[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>ClCCl.CCN(C(C)C)C(C)C>[CH2:31]([C@H:30]([N:38]([CH2:39][C:40]1[CH:41]=[CH:42][C:43]([CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:44][CH:45]=1)[C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:14])=[CH:13][CH:12]=1)[C:29]([N:26]1[CH2:25][CH2:24][N:23]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:28][CH2:27]1)=[O:51])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 6880704-(Trifluoromethyl)cinnamic acidHCID 598082551-(4-benzyl-piperazin-1-yl)-(S)-2-(4-pentyl-benzylamino)-3-phenyl-propan-1-one

Produkt 1

HCID 67005150N-[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(4-pentyl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamideAusbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

In an inert atmosphere, trans-4-trifluoromethyl-cinnamic acid (21.4 mg, 0.099 mmol) was dissolved in 2 mL dichloromethane followed by the addition of 1-chloro-N,N-2-trimethylpropenyl amine (16.4 μl, 0.122 mmol). Stirring was continued at rt for 1 h. This solution was then added to a solution of 1-(4-benzyl-piperazin-1-yl)-(S)-2-(4-pentyl-benzylamino)-3-phenyl-propan-1-one (43.5 mg, 0.09 mmol) in dichloromethane (1 mL) and Hünig's base (39 μl). The resulting mixture was stirred for 1 h at rt, followed by the addition of water (3 mL). The layers were separated. The aq. layer was extracted with dichloromethane (2×2 mL) and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by prep. TLC (silicagel, heptane/EtOAc=1/1) to give 36.1 mg (58%) of N—[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(4-pentyl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide. LC-MS: tR=1.02 min; [M+H]+=682.48.

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 1 h at rt
  2. customThe layers were separated
  3. extractionThe aq. layer was extracted with dichloromethane (2×2 mL)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-98c6c7f654ca4cba9463d0ddf55e7b70
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067419B2

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