Piperidine → 1-(4-Bromo-2-fluorobenzyl)piperidine

HRID 1505895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505895
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([F:10])[CH:3]=1

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 534861121-(4-Bromo-2-fluorobenzyl)piperidineAusbeute 106,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a pre-stirred solution of 4-bromo-2-fluorobenzaldehyde (1.82 g, 9.0 mmol) and piperidine (0.97 mL, 9.9 mmol) in DCM (40 mL) at 0° C. was added sodium triacetoxyborohydride (2.85 g, 13.4 mmol) in portions. The reaction mixture was allowed to warm to ambient temperature and stirred for an additional 14 h. The reaction was quenched by the addition of water (30 mL) and extracted with ethyl acetate (75 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as a colourless oil (2.6 g, 84%) that was used in the next step without further purification. NMR (CDCl3, 400 MHz): 7.33-7.17 (m, 3H), 3.49 (d, J=1.6 Hz, 2H), 2.43-2.33 (m, 4H), 1.61-1.53 (m, 4H), 1.46-1.38 (m, 2H).

Aufarbeitung

  1. customThe reaction was quenched by the addition of water (30 mL)
  2. extractionextracted with ethyl acetate (75 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9977893c039d4400bf6dd7d83a221e3a
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216980B2

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