Chloroform → 1-(4-chlorobenzyl)-4-[[N-(3,5-bis(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine

HRID 133596

Reaktionsgleichung

Reaktionsgleichung von HRID 133596
ClCCl.[F:4][C:5]([F:20])([F:19])[C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:9](Cl)=[O:10].[Cl:21][C:22]1[CH:40]=[CH:39][C:25]([CH2:26][N:27]2[CH2:32][CH2:31][CH:30]([CH2:33][NH:34][C:35](=[O:38])[CH2:36][NH2:37])[CH2:29][CH2:28]2)=[CH:24][CH:23]=1.C(Cl)(Cl)Cl>CO>[Cl:21][C:22]1[CH:40]=[CH:39][C:25]([CH2:26][N:27]2[CH2:28][CH2:29][CH:30]([CH2:33][NH:34][C:35](=[O:38])[CH2:36][NH:37][C:9](=[O:10])[C:8]3[CH:7]=[C:6]([C:5]([F:20])([F:19])[F:4])[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=3)[CH2:31][CH2:32]2)=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 6344Dichloromethane2×HCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 184261551-(4-Chlorobenzyl)-4-((glycylamino)methyl}piperidine

Produkt 1

HCID 184262011-(4-chlorobenzyl)-4-[[N-(3,5-bis(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A dichloromethane (1 mL) solution of 3,5-bis(trifluoromethyl)benzoyl chloride (0.058 mmol) was added to a mixture of 1-(4-chlorobenzyl)-4-[(glycylamino)methyl]piperidine (0.050 mmol) with chloroform (0.2 mL), a piperidinomethylpolystyrene (58 mg) and dichloromethane (0.75 mL). The resulting reaction mixture was stirred at room temperature for 2 hours, and methanol (1.0 mL) was then added to the obtained mixture. The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was loaded onto a Varian™ SCX column and washed with methanol (16 mL). The obtained crude product was eluted with a 2 M methanol solution of NH3 (6 mL) and concentrated to thereby provide 1-(4-chlorobenzyl)-4-[[N-(3,5-bis(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. No. 1213) (24.0 mg, 90%). The purity was determined by RPLC/MS (100%). ESI/MS m/e 536.2 (M++H, C24H24ClF6N3O2).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  3. washwashed with methanol (16 mL)
  4. customThe obtained crude product
  5. washwas eluted with a 2 M methanol solution of NH3 (6 mL)
  6. concentrationconcentrated to thereby provide 1-(4-chlorobenzyl)-4-[[N-(3,5-bis(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. No

Quellen und Nachweise

ORD-Eintrag
ord-8a61569f96114cb8bb403549dc6d81ad
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390830B1

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