4-Bromophenetole → [1-(4-Ethoxy-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester

HRID 511149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 511149
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].Br[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][CH:18]=1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2(C)CC=CC=C2C2C=CC=CC=2)CCCCC1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][CH:18]=2)[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 685234-BromophenetoleHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 23676156Sodium t-butoxideHCID 66672255Dicyclohexyl-(1-methyl-2-phenylcyclohexa-2,4-dien-1-yl)phosphane

Produkt 1

HCID 58576345[1-(4-Ethoxy-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl esterAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A suspension of piperidin-4-ylmethyl-carbamic acid tert-butyl ester (1.0 g; 4.67 mmol), 1-bromo-4-ethoxy-benzene (1.87 g; 9.33 mmol), tris(dibenzylideneacetone)dipalladium (174 mg; 0.19 mmol), sodium tert-butoxide (524 mg; 4.67 mmol) and 2-(dicyclohexylphosphino)-2-methylbiphenyl (135 mg; 0.37 mmol) in toluene (30 mL) is thoroughly flushed with argon. The reaction mixture is then heated at 70° C. for 17 hours. After dilution with ethyl acetate (50 mL), the suspension is filtered over Celite and the filtrate is washed with aq. sat ammonium chloride (2×25 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue obtained is then further purified by flash column chromatography on silica gel (Ethyl acetate:heptane 25:75) to afford the desired product (963 mg; 2.88 mmol).

Aufarbeitung

  1. customis thoroughly flushed with argon
  2. filtrationAfter dilution with ethyl acetate (50 mL), the suspension is filtered over Celite
  3. washthe filtrate is washed
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis then further purified by flash column chromatography on silica gel (Ethyl acetate:heptane 25:75)

Quellen und Nachweise

ORD-Eintrag
ord-001c3d7412484f609c55fbf62e56dd9f
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096524B2

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