Triethylamine → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-(3-pyridylmethylamino)-2-butynyl]-2-(2-naphthylmethyl)piperazine trihydrochloride

HRID 584191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 584191
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][Cl:18])[CH2:10][C@H:9]1[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)=[O:7].[NH2:39][CH2:40][C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1.C(N(CC)CC)C>C(#N)C>[ClH:18].[ClH:18].[ClH:18].[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][NH:39][CH2:40][C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)[CH2:10][C@H:9]1[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)=[O:7]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 53862488(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(4-chloro-2-butynyl)-2-(2-naphthylmethyl)piperazine

Produkt 1

HCID 86596428(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-(3-pyridylmethylamino)-2-butynyl]-2-(2-naphthylmethyl)piperazine trihydrochlorideAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(4-chloro-2-butynyl)-2-(2-naphthylmethyl)piperazine (200 mg), 3-(aminomethyl)pyridine (47 mg), and triethylamine (0.08 ml) in acetonitrile (2 ml) was stirred under reflux for 3 hours and evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (10 ml) using dichloromethane-methanol (30:1) as eluent. The obtained oil was dissolved in ethyl acetate and treated with a solution of,4N hydrogen chloride in ethyl acetate. The mixture was evaporated under reduced pressure to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-(3-pyridylmethylamino)-2-butynyl]-2-(2-naphthylmethyl)piperazine trihydrochloride (60 mg) as a powder.

Aufarbeitung

  1. temperatureunder reflux for 3 hours
  2. customevaporated under reduced pressure
  3. customThe obtained residue was purified by column chromatography on silica gel (10 ml)
  4. dissolutionThe obtained oil was dissolved in ethyl acetate
  5. additiontreated with a solution of,4N hydrogen chloride in ethyl acetate
  6. customThe mixture was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9dd6b92cc1cd44c3bbbba11f3b883b51
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924278B2

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