Phenyl isocyanate → 1-(4-benzylbenzyl)-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine
Reaktionsgleichung
CS(Cl)(=O)=O.C1CCNCC1.[CH2:12]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]O)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F:27][C:28]([F:50])([F:49])[C:29]1[CH:30]=[C:31]([CH:46]=[CH:47][CH:48]=1)[C:32]([NH:34][CH2:35][C:36]([NH:38][CH2:39][CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=[O:37])=[O:33].C1(N=C=O)C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:12]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:43]2[CH2:44][CH2:45][CH:40]([CH2:39][NH:38][C:36](=[O:37])[CH2:35][NH:34][C:32](=[O:33])[C:31]3[CH:46]=[CH:47][CH:48]=[C:29]([C:28]([F:50])([F:49])[F:27])[CH:30]=3)[CH2:41][CH2:42]2)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
A chloroform (1.0 mL) solution of methanesulfonyl chloride (4.2 mg, 0.037 mmol) and a (piperidinomethyl)polystyrene (54 mg, 2.7 mmol base/g resin) were added to a chloroform (1.0 mL) solution of 4-(benzyl)benzyl alcohol (8.7 mg, 0.044 mmol), and the resulting mixture was stirred at 25° C. for 15 hours. 4-[[N-(3-(Trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (15.1 mg, 0.044 mmol) and KI (2 mg) were then added to the reaction mixture, and the resulting mixture solution was further stirred at 65° C. for 5 hours. Phenyl isocyanate (5.2 mg) was added to the cooled reaction mixture, and the obtained mixture was stirred at 25° C. for 1 hour. The resulting reaction mixture was loaded onto a Varian™ SCX column and washed with methanol (20 mL). The obtained crude product was eluted with a 2 M methanol solution of NH3 (5 mL) and concentrated to thereby afford 1-(4-benzylbenzyl)-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. No. 926) as an off-white oil (5.6 mg, 29%). The purity was determined by RPLC/MS (94%). ESI/MS m/e 524.1 (M++H, C30H32F3N3O2).
Aufarbeitung
- stirringthe resulting mixture solution was further stirred at 65° C. for 5 hours
- stirringthe obtained mixture was stirred at 25° C. for 1 hour
- customThe resulting reaction mixture
- washwashed with methanol (20 mL)
- customThe obtained crude product
- washwas eluted with a 2 M methanol solution of NH3 (5 mL)
- concentrationconcentrated to thereby afford 1-(4-benzylbenzyl)-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. No
Quellen und Nachweise
- ORD-Eintrag
- ord-958bb623c80747ba8b9cd7069cbb9bf0
- Quelldatensatz
- uspto-grants-2008_06
- Patentnummer
- US07390830B1
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