4-Butoxybenzaldehyde → HCID 59808329, Verbindung

HRID 563145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 563145
Cl.[NH2:2][C@@H:3]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5].CCN(C(C)C)C(C)C.[CH2:35]([O:39][C:40]1[CH:47]=[CH:46][C:43]([CH:44]=O)=[CH:42][CH:41]=1)[CH2:36][CH2:37][CH3:38].[BH4-].[Na+]>CO.O>[CH2:12]([N:9]1[CH2:10][CH2:11][N:6]([C:4](=[O:5])[C@@H:3]([NH:2][CH2:44][C:43]2[CH:46]=[CH:47][C:40]([O:39][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:41][CH:42]=2)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:7][CH2:8]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 798134-ButoxybenzaldehydeHCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 67005485HCID 67005485, Verbindung

Produkt 1

HCID 59808329HCID 59808329, VerbindungAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-Amino-1-(4-benzyl-piperazin-1-yl)-(S)-3-phenyl-propan-1-one hydrochloride (500 mg, 1.26 mmol) were dissolved in MeOH (5 mL), DIPEA (359 mg, 2.77 mmol) and 4-n-butoxybenzaldehyde (226 mg, 1.26 mmol) was added and the mixture was heated to reflux for 2 h, cooled again to rt followed by slow addition of sodium borohydride (48 mg, 1.26 mmol) in portions. Stirring was continued for 15 min. Water (1 mL) was added and the solvents were removed under reduced pressure. The residue was taken up in diethylether (5 mL), washed with 10% aq. citric acid (5 mL) and water (5 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to give 411 mg (67%) of 1-(4-benzyl-piperazin-1-yl)-2-(4-butoxy-benzylamino)-(S)-3-phenyl-propan-1-one. LC-MS: tR=0.74 min; [M+H]+=486.43.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. customthe solvents were removed under reduced pressure
  4. washwashed with 10% aq. citric acid (5 mL) and water (5 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-edc50b27b88c4e86aea8c5d833b9b7b9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067419B2

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