Potassium Carbonate → Tert-butyl 4-(2-(3,3-diphenylpropylamino)ethyl)piperidine-1-carboxylate

HRID 2190297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190297
Br[CH2:2][CH2:3][CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:17][CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:5]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3][CH2:2][NH:17][CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 883331,1'-(3-Bromopropylidene)bisbenzeneHCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

Produkt 1

HCID 57586396Tert-butyl 4-(2-(3,3-diphenylpropylamino)ethyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

3-bromo-1,1-diphenylpropane (2.6 g, 9 mmol) and tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate (4.7 g, 21 mmol) were mixed together in acetonitrile (100 ml) and potassium carbonate (1.3 g, 9 mmol) was added. The resulting mixture was heated to 65° C. with stirring under N2 overnight. After that time the mixture was cooled and concentrated under reduced pressure. The residue was partitioned between DCM and water. The DCM layer was washed with water, dried over MgSO4 and concentrated under reduced pressure to give the crude product as a clear oil. The crude product was purified by combiflash (0-10% MeOH/DCM) to give tert-butyl 4-(2-(3,3-diphenylpropylamino)ethyl)piperidine-1-carboxylate 48

Aufarbeitung

  1. temperatureAfter that time the mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between DCM and water
  4. washThe DCM layer was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product as a clear oil
  8. customThe crude product was purified by combiflash (0-10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-af392d7a01494aa1af414039b10d11c3
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324396B2

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