Ethanol → HCID 117599397, Verbindung

HRID 1466123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1466123
Cl.[CH3:2][CH:3]1[NH:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[C:4]1=[O:20].[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]=O)=[CH:26][CH:25]=1)([O-:23])=[O:22].C(O)C.C([BH3-])#N.[Na+]>C(OCC)(=O)C>[CH3:2][CH:3]1[N:8]([CH2:31][CH2:30][C:27]2[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:29][CH:28]=2)[CH2:7][CH2:6][N:5]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)[C:4]1=[O:20]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 11744988(4-Nitrophenyl)acetaldehydeHCID 89525148HCID 89525148, Verbindung

Produkt 1

HCID 117599397HCID 117599397, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 3-Methyl-1-[2-(4-nitrophenyl)ethyl]piperazin-2-one hydrochloride (38 mg, 0.13 mmol) and (4-Nitrophenyl)acetaldehyde (31 mg, 0.19 mmol) was added_titanium(IV) isopropoxide (0.37 mL, 1.3 mmol). After stirring the mixture at RT for 15 minutes, ethanol (2 mL) and sodium cyanoborohydride (80 mg, 1.3 mmol) were added to the reaction. The mixture was allowed to stir at RT for 16 hours. The reaction was diluted with ethyl acetate, washed with brine, dried over sodium sulfate, and concentrated to give the crude title product. The title product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 413 [M+1]+.

Aufarbeitung

  1. stirringto stir at RT for 16 hours
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-50a611d60d1c4c25acc76c665083b91e
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999990B2

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