Carbon tetrabromide → 4-[4-(2-Bromo-ethyl)-4-hydroxy-piperidin-1-yl]-2-trifluoromethyl-benzonitrile

HRID 1919306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1919306
[OH:1][C:2]1([CH2:20][CH2:21]O)[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:49]>ClCCl>[Br:49][CH2:21][CH2:20][C:2]1([OH:1])[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 11205Carbon tetrabromideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 675011244-[4-Hydroxy-4-(2-hydroxy-ethyl)-piperidin-1-yl]-2-trifluoromethyl-benzonitrile

Produkt 1

HCID 675025684-[4-(2-Bromo-ethyl)-4-hydroxy-piperidin-1-yl]-2-trifluoromethyl-benzonitrileAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of compound 27a (687 mg, 2.09 mmol) in anhydrous dichloromethane (10 mL) at 0° C. under argon were added potassium carbonate (1.16 g, 8.39 mmol), triphenylphosphine (1.1 g, 4.19 mmol) and carbon tetrabromide (1.39 g, 4.19 mmol). The solution was allowed to return to room temperature and stirred for 1 hr. The resulting solution was diluted with dichloromethane (50 mL) and filtered on a cotton plug. Purification of the resulting crude product by flash chromatography using ethyl acetate/hexane (2:8) gave the desired compound 28a (470 mg, 57%). 1H NMR (400 MHz, MeOD) δ: 1.72 (m, 4H), 2.11 (m, 2H), 3.37 (m, 2H), 3.54 (m, 2H), 3.77 (m, 2H), 7.18 (dd, 1H, J1=6.26 Hz, J2=2.62 Hz), 7.27 (d, 1H, J=2.07 Hz), 7.69 (d, 1H, J=8.83 Hz).

Aufarbeitung

  1. customto return to room temperature
  2. filtrationfiltered on a cotton plug
  3. customPurification of the resulting crude product by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b253706a7dfa461cbf2f28842e52ab38
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168627B2

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