Triethylamine → Methyl 3-chloro-4-({[3-({[(1r)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]carbonyl}amino)benzoate

HRID 1691680

Reaktionsgleichung

Reaktionsgleichung von HRID 1691680
[C:1]1([C@H:11]([NH:13][CH2:14][CH:15]2[CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][CH2:18][NH:17][CH2:16]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:34][C:35]1[CH:36]=[C:37]([CH:42]=[CH:43][C:44]=1[NH:45][C:46](OC1C=CC([N+]([O-])=O)=CC=1)=[O:47])[C:38]([O:40][CH3:41])=[O:39]>C1COCC1>[Cl:34][C:35]1[CH:36]=[C:37]([CH:42]=[CH:43][C:44]=1[NH:45][C:46]([N:17]1[CH2:18][CH2:19][CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]([CH2:14][NH:13][C@@H:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH3:12])[CH2:16]1)=[O:47])[C:38]([O:40][CH3:41])=[O:39]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 59178736(1R)-1-(1-naphthyl)-N-[(4-phenylpiperidin-3-yl)methyl]ethaneamineHCID 59178754Methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate

Produkt 1

HCID 59178780Methyl 3-chloro-4-({[3-({[(1r)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]carbonyl}amino)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 217 mg of the crude product of (1R)-1-(1-naphthyl)-N-[(4-phenylpiperidin-3-yl)methyl]ethaneamine and 0.175 mL of triethylamine in 4.0 mL of THF was added 243 mg of methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate. After stirring at room temperature overnight, the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 214 mg of methyl 3-chloro-4-({[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]carbonyl}amino)benzoate.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d001c5ae4a5b4faeac4dbbd6c5f4e121
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153658B2

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