Potassium Iodide → 4-Boc-1-(2-methoxy-ethyl)-piperidin-4-ylamine

HRID 1865199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1865199
[C:1]([CH:8]1[CH2:13][CH2:12][N:11](N)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:23][O:24][CH2:25][CH2:26]Br.C(#[N:30])C>O>[C:1]([C:8]1([NH2:30])[CH2:13][CH2:12][N:11]([CH2:26][CH2:25][O:24][CH3:23])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

7

Edukt 5

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 21899493Tert-butyl 1-aminopiperidine-4-carboxylate

Produkt 1

HCID 690188804-Boc-1-(2-methoxy-ethyl)-piperidin-4-ylamineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-boc-aminopiperidine (11, 10.0 g, 50 mmol), potassium carbonate (6.5 g, 47 mmol), potassium iodide (7.7 g, 46 mmol), 2-bromoethyl methyl ether (4.4 mls, 46 mmol), and acetonitrile (100 mls) was heated to reflux for 3 hrs. After cooling to room temperature, the reaction mixture was poured into H2O and extracted with EtOAc (4×). The combined EtOAc extractions were washed with sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo to give 4-boc-1-(2-methoxy-ethyl)-piperidin-4-ylamine (12, 12.0 g, 99%) which was used in the next reaction without further purification. LC/MS Calcd for [M+H]+ 259, found 259.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 hrs
  3. extractionextracted with EtOAc (4×)
  4. extractionThe combined EtOAc extractions
  5. washwere washed with sat'd NaCl (1×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f34ba5a21ed1432b9d8cf303c2031317
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07626031B2

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