N,N-Dimethylpiperidin-4-amine → 1-(5-bromopyridin-2-yl)-N,N-dimethylpiperidin-4-amine

HRID 423390

Reaktionsgleichung

Reaktionsgleichung von HRID 423390
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[CH3:9][N:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[CH3:11]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:15]2[CH2:16][CH2:17][CH:12]([N:10]([CH3:11])[CH3:9])[CH2:13][CH2:14]2)=[N:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 417391N,N-Dimethylpiperidin-4-amineHCID 27831685-Bromo-2-fluoropyridine

Produkt 1

HCID 582995761-(5-bromopyridin-2-yl)-N,N-dimethylpiperidin-4-amineAusbeute 92,3 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Mix 5-bromo-2-fluoro-pyridine (1.00 g, 5.68 mmol) and N,N-dimethyl-piperidin-4-yl-amine (1.50 g, 11.70 mmol) together and heat to 80° C. for 64 h. Partition the reaction between CH2Cl2 (5 mL) and 1N NaOH (8 mL). Collect the organic phase and extract the aqueous phase with additional CH2Cl2 (2×20 mL). Combine the organic solutions, then dry, filter, and concentrate. Purify the crude material by flash chromatography using an eluent of 5% MeOH (2N NH3)/CH2Cl2 to give 1.49 g (92%) of the title compound as a white solid. 1H NMR (CDCl3) δ 1.46 (dq, 2H, J=4.0, 11.8 Hz), 1.86 (br d, 2H, J=12.8 Hz), 2.26 (s, 6H), 2.32 (m, 1H), 2.80 (dt, 2H, J=2.7, 12.8 Hz), 4.23 (br d, 2H, J=13.2 Hz), 6.53 (d, 1H, J=8.9 Hz), 7.46 (dd, 1H, J=2.8, 9.0 Hz), 8.13 (d, 1H, J=2.6 Hz).

Aufarbeitung

  1. customPartition
  2. customthe reaction between CH2Cl2 (5 mL) and 1N NaOH (8 mL)
  3. customCollect the organic phase
  4. extractionextract the aqueous phase with additional CH2Cl2 (2×20 mL)
  5. customCombine the organic solutions, then dry
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the crude material by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cbb2a61260084d44b4ea4684921d9062
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101764B2

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