Potassium Carbonate → N-[4-(1-{3-[(diphenylacetyl)amino]propyl}4-piperidinyl)phenyl]-2-methylpropanamide

HRID 1269171

Reaktionsgleichung

Reaktionsgleichung von HRID 1269171
[CH3:1][CH:2]([CH3:18])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:4].Br[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:38])[CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>CN(C=O)C>[C:26]1([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:24]([NH:23][CH2:22][CH2:21][CH2:20][N:15]2[CH2:16][CH2:17][CH:12]([C:9]3[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH:2]([CH3:18])[CH3:1])=[CH:7][CH:8]=3)[CH2:13][CH2:14]2)=[O:38])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 1859152-NaphthylalanineHCID 21957140N-(3-bromopropyl)-2,2-diphenylacetamideHCID 219572582-methyl-N-[4-(4-piperidinyl)phenyl]propanamide

Produkt 1

HCID 21957230N-[4-(1-{3-[(diphenylacetyl)amino]propyl}4-piperidinyl)phenyl]-2-methylpropanamideAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-methyl-N-[4-(4-piperidinyl)phenyl]propanamide (50.0 mg, 2.0 mmol), N-(3-bromopropyl)-2,2-diphenylacetamide (64.2 mg, 0.2 mmol), K2CO3 (55.0 mg, 4.0 mmol), and Nal (45.0 mg, 0.3 mmol) in 2 mL of DMF was stirred at room temperature for 10 minutes followed by heating to 80–90° C. for 12 h. The reaction mixture was cooled to room temperature and purified by preparative TLC (silica gel, EtOAc/NH3 (2 M in MeOH); 95:5) to afford N-[4-(1-{3-[(diphenylacetyl)amino]propyl}-4-piperidinyl)phenyl]-2-methylpropanamide as a colorless oil (15.7 mg, 32%): ESMS m/e: 498.3 (M+H)+.

Aufarbeitung

  1. temperatureby heating to 80–90° C. for 12 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompurified by preparative TLC (silica gel, EtOAc/NH3 (2 M in MeOH); 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-21feb498188149bebfe3b598aa13e558
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199135B2

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